4530-20-5

Basic information

• Product Name: BOC-Glycine
• Synonyms: BOC-GLYCINE-OH;BOC-GLY;BOC-GLYCINE;BOC-GLY-OH;BOC-L-GLY;BOC-AMINOXYACETIC ACID;N-T-BOC-GLYCINE;N-T-BUTOXYCARBONYL-GLYCINE
• CAS NO: 4530-20-5
• Molecular Formula: C₇H₁₃NO₄
• Molecular Weight: 175.18
• EINECS: 224-864-5
• Product Categories: Protected Amino Acids;AMINOACIDS DERIVATIVES;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Amino Acids;Glycine [Gly, G];Boc-Amino Acids and Derivative;Amino Acids 13C, 2H, 15N;Absolute Configuration Determination (Exciton Chirality CD Method);Amino Acids (N-Protected);Analytical Chemistry;Biochemistry;Boc-Amino Acids;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Methodfor (for Monofunctional Compounds);Boc-Amino acid series;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 4530-20-5.mol
• Article Data: 180

Chemical Properties

• Melting Point: 86-89 °C(lit.)
• Boiling Point: 306.47°C (rough estimate)
• Flash Point: 144.9 °C
• Appearance: White to off-white/Powder
• Density: 1.2843 (rough estimate)
• Vapor Pressure: 9.08E-05mmHg at 25°C
• Refractive Index: 1.4353 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 4.00±0.10(Predicted)
• Water Solubility: soluble
• BRN: 1101514
• CAS DataBase Reference: BOC-Glycine(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-Glycine(4530-20-5)
• EPA Substance Registry System: BOC-Glycine(4530-20-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41-36/37/38-20/21/22
• Safety Statements: 26-36/37/39-39-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4530-20-5(Hazardous Substances Data)

Usage

Chemical Properties

White To Off-White Powder

Uses

Different sources of media describe the Uses of 4530-20-5 differently. You can refer to the following data:
1. BOC-Glycine is used in the composition of drugs containing Ketoprofen, and Sodium hyaluronate as antiinflammatory agents.
2. Boc-Gly-OH can be used:For the esterification reaction to synthesize N-Boc amino acid esters for peptide chemistry.For the synthesis of tripeptide H-Gly-Pro-Glu-OH, analogs of neuroprotective drugs.As a promoter for the allylation of hydrazones and isatin.

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 4393, 1975 DOI: 10.1016/S0040-4039(00)91133-X

InChI:InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)/p-1

Synthetic route

di-tert-butyl dicarbonate (24424-99-5) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 20℃; for 12h;	100%
Stage #1: glycine With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃;	100%
With sodium hydroxide In 1,4-dioxane	100%

2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate (83316-95-4) → BOC-glycine (4530-20-5) + acetophenone (98-86-2)

Conditions	Yield
With N,N,N',N'-tetramethyl-o-phenylenediamine In acetonitrile for 2h; Irradiation;	A 100% B n/a

tert-butoxycarbonylamino-acetic acid 4-tert-butyl-benzyl ester → BOC-glycine (4530-20-5) + 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal for 3h;	A 100% B n/a

(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl (tert-butoxycarbonyl)glycinate → BOC-glycine (4530-20-5) + C16H10O3S (1033736-87-6)

Conditions	Yield
In chloroform-d1 for 0.25h; Solvent; Photolysis; Inert atmosphere;	A 97% B n/a

glycine (56-40-6) + BOC derivative → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 8h;	95%

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium hydroxide In water; acetone at 25℃; for 12h;	94%

(N-hydroxy-5-norbornene-2,3-diformylimino)tert-butyl ester (64205-15-8) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With tertiary amine In 1,4-dioxane; water for 3h;	85%

tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate (909114-65-4) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With triethylamine In methanol at 20℃; for 0.5h;	85%

4-nitrobenzyl N-(tert-butoxycarbonyl)glycinate (79113-14-7) → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium dithionite; sodium carbonate In acetonitrile	80%

glycine (56-40-6) + 1-tert-butoxycarbonyloxybenzotriazole (89037-64-9) → BOC-glycine (4530-20-5)

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 0.166667h; Ambient temperature;	80%

2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate (83316-95-4) → BOC-glycine (4530-20-5) + (tert-butoxycarbonyl)glycine hydrazide (6926-09-6)

Conditions	Yield
With hydrazine hydrate In methanol Product distribution;	A 75% B 12%

N-Boc-glycine 2-(2-acetylphenyl)-1-methylethyl ester (618068-89-6) → BOC-glycine (4530-20-5)

Conditions	Yield
In acetonitrile for 3h; Photolysis;	73%

(E)-3-methoxyallyl 2-((tert-butoxycarbonyl)amino)acetate (1080004-01-8) → BOC-glycine (4530-20-5)

Conditions	Yield
With zinc(II) chloride; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	59%
With potassium hexamethylsilazane; zinc(II) chloride In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	54%

tert-Butoxycarbonylamino-acetic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester (42721-06-2) + glycine ethyl ester hydrochloride (5680-79-5) → BOC-glycine (4530-20-5) + N-tert-butoxycarbonyl glycyl glycine methyl ester (53487-98-2)

Conditions	Yield
With 4-methyl-morpholine In N,N-dimethyl-formamide at 38℃; for 96h;	A n/a B 57%

glycine ethyl ester hydrochloride (5680-79-5) + 2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-glycyl)-β-D-glucopyranose (35909-78-5) → BOC-glycine (4530-20-5) + N-tert-butoxycarbonyl glycyl glycine methyl ester (53487-98-2) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (4132-28-9, 4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5)

Conditions	Yield
With 4-methyl-morpholine In N,N-dimethyl-formamide at 38℃; for 96h;	A n/a B 55% C n/a

t-butyl malonate (541-16-2) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium carbonate In water; acetonitrile at -5 - 20℃;	35%

Glycine tert-butyl ester (6456-74-2) + 2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate (83316-95-4) → BOC-glycine (4530-20-5) + Boc-glycylglycine tert-butyl ester (5845-68-1)

Conditions	Yield
In ethyl acetate for 24h; Product distribution; Ambient temperature;	A 10% B 30%

tert-Butyl 4-nitrophenyl carbonate (13303-10-1) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium hydroxide; tert-butyl alcohol

phosgene (75-44-5) + GlyOEt*HCl (459-73-4) → BOC-glycine (4530-20-5)

Conditions	Yield
With toluene Erwaermen des Reaktionsprodukts mit tert-Butylalkohol und anschliessenden Hydrolyse;

tert-butyl alcohol (75-65-0) + Glycine ethyl ester isocyanate (2949-22-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With triethylamine Behandeln des Reaktionsprodukts mit wss.NaOH und Dioxan;

tert-butyl chloroformate (24608-52-4) + glycine (56-40-6) → BOC-glycine (4530-20-5)

Conditions	Yield
With sodium hydroxide

BOC-glycine (4530-20-5) + benzylamine (100-46-9) → Boc-glycine-benzylamide (19811-52-0)

Conditions	Yield
Stage #1: BOC-glycine; benzylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0166667h; Stage #2: With HATU for 18h;	100%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;	99%

BOC-glycine (4530-20-5) + methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) → Nα-tert-butoxycarbonylglycyl-Nε-benzyloxycarbonyl-L-lysine methyl ester (32689-62-6)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at -20 - 20℃; for 4h; Acylation;	100%
Stage #1: BOC-glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Cooling with ice; Stage #2: methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	92.2%
(i) Et3N, ClCO2iBu, (ii) /BRN= 3578476/, Et3N; Multistep reaction;
With 4-methyl-morpholine; triethylamine; isobutyl chloroformate 1) THF, -10 deg C, 15 min, 2) THF, 12 h; Yield given. Multistep reaction;

BOC-glycine (4530-20-5) + L-alanine benzyl ester p-toluenesulfonate (42854-62-6) → Boc-Gly-Ala-OBzl (63649-08-1)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine	100%
With TEA; diphenyl phosphoryl azide In N,N-dimethyl-formamide 1.) 0 deg C, 4 h; 2.) r.t., overnight;	85%
Stage #1: BOC-glycine; L-alanine benzyl ester p-toluenesulfonate With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;

BOC-glycine (4530-20-5) + benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → (S)-1-(2-tert-butoxycarbonylaminoacetyl)pyrrolidine-2-carboxylic acid benzyl ester (29776-78-1)

Conditions	Yield
With benzotriazol-1-ol; triethylamine In chloroform	100%
With benzotriazol-1-ol; triethylamine In chloroform	100%
With benzotriazol-1-ol; triethylamine In chloroform	100%

BOC-glycine (4530-20-5) + L-valine benzyl ester p-toluenesulfonate salt (16652-76-9) → N-t-butoxycarbonylglycyl-L-valine benzyl ester (66415-00-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine	100%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	94%
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) 0 deg C, 2.) overnight, 4 deg C;	89%
With 4-methyl-morpholine; isobutyl chloroformate 1.) THF, -15 deg C, 2.) DMF, a) -15 deg C, 30 min, b) r.t., 30 min.; Yield given. Multistep reaction;

BOC-glycine (4530-20-5) + (-)-8-phenylmenthol (65253-04-5) → (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate (117681-86-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 13h;	100%
Stage #1: BOC-glycine With dmap; dicyclohexyl-carbodiimide In dichloromethane at -30℃; for 0.166667h; Stage #2: (-)-8-phenylmenthol In dichloromethane for 20h; Heating;	96%
With dmap; dicyclohexyl-carbodiimide	93%

BOC-glycine (4530-20-5) → 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2)

Conditions	Yield
Stage #1: BOC-glycine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at -15℃; for 1h;	100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane for 4h; Ambient temperature;	88%
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 0℃; for 2h;	77.1%

BOC-glycine (4530-20-5) + benzyl bromide (100-39-0) → tert-butoxycarbonylamino-acetic acid benzyl ester (54244-69-8)

Conditions	Yield
Stage #1: BOC-glycine With caesium carbonate In methanol pH=7; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 5h; Further stages.;	100%
Stage #1: BOC-glycine With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0℃; for 18h; Further stages;	100%
With triethylamine In N,N-dimethyl-formamide at 25℃; for 5h;	54%
With caesium carbonate 1) MeOH, water, pH 7.0, 2) DMF, 5 h; Yield given. Multistep reaction;
With sodium iodide In acetone for 2h; Reflux; Inert atmosphere;

BOC-glycine (4530-20-5) + ethyl iodide (75-03-6) → N-(tert-buytoxycarbonyl)-N-ethylglycine (149794-10-5)

Conditions	Yield
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: In tetrahydrofuran at 0℃;	100%
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: With citric acid In water pH=2 - 3;	100%
Stage #1: BOC-glycine; ethyl iodide With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: With citric acid In water pH=2 - 3;	100%

BOC-glycine (4530-20-5) + allyl bromide (106-95-6) → allyl 2-(tert-butoxycarbonylamino)acetate (124373-83-7)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 16h;	100%
With N-ethyl-N,N-diisopropylamine for 0.666667h; Reflux;	91%
With caesium carbonate In acetonitrile	90%

BOC-glycine (4530-20-5) + aniline (62-53-3) → N-glycyl>aniline (27904-92-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 5h;	100%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;	99%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 6h;	96.9%

BOC-glycine (4530-20-5) + isobutyl chloroformate (543-27-1) → N-(t-butoxycarbonyl)glycyl i-butyl carbonate (66866-43-1)

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at -15℃; for 0.0833333h;	100%
With 4-methyl-morpholine In tetrahydrofuran at -20℃; for 0.05h;

BOC-glycine (4530-20-5) + tetrakis-5,10,15,20-(o-aminophenyl)porphyrin (52199-35-6) → α,α,α,α-5,10,15,20-tetrakis-(2-(N-[(2-t-butylcarbamoyl)ethanamide]phenyl))porphyrin

Conditions	Yield
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 50h; Condensation;	100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Inert atmosphere; Cooling with ice;	62%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

BOC-glycine (4530-20-5) + H-Ala-Glu(OBzl)-OBzl hydrochloride → Boc-Gly-Ala-Glu(OBzl)-OBzl (125274-43-3)

Conditions	Yield
Stage #1: H-Ala-Glu(OBzl)-OBzl hydrochloride With triethylamine In dichloromethane Hydrolysis; Stage #2: BOC-glycine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 14h; Condensation;	100%

BOC-glycine (4530-20-5) + phenethylamine (64-04-0) → tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate (613675-75-5)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 0 - 20℃; Acylation;	100%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 72h;	94%
Stage #1: BOC-glycine With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: phenethylamine In dichloromethane for 16h;	81%
Stage #1: BOC-glycine With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: phenethylamine In N,N-dimethyl-formamide at 20℃;	72%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 23℃; for 4h; Inert atmosphere;	71%

1-aza-18-crown-6 (33941-15-0) + BOC-glycine (4530-20-5) → [2-oxo-2-(1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl)-ethyl]-carbamic acid tert-butyl ester (394208-14-1)

Conditions	Yield
With bis(trichloromethyl) carbonate; lutidine In tetrahydrofuran at 25 - 50℃; for 2h;	100%
With 2,6-dimethylpyridine; bis(trichloromethyl) carbonate In tetrahydrofuran Inert atmosphere;

BOC-glycine (4530-20-5) + 4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino}benzyl alcohol (172611-73-3) → tert-butoxycarbonylamino-acetic acid 4-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-3-methyl-butylamino]-benzyl ester

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	100%

BOC-glycine (4530-20-5) + 4,6-O-di(tert-butyl)silanediyl-D-glucal (191593-14-3) → 3-O-(N-tert-butoxycarbonyl-2'-amino-ethanoyl)-4,6-O-di-tert-butylsilanediyl-D-glucal (848359-00-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	100%

BOC-glycine (4530-20-5) + Propargylamine (2450-71-7) → tert-butyl (2-oxo-2-(prop-2-yn-1-ylamino)ethyl)carbamate (847490-49-7)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; Inert atmosphere;	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;	99%
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In acetonitrile at 20℃;	96%

BOC-glycine (4530-20-5) + anthranilic acid (118-92-3) + 2-methoxyethylamine (109-85-3) → 2-aminomethyl-3-(2-methoxyethyl)-3H-quinazolin-4-one

Conditions	Yield
Stage #1: BOC-glycine; anthranilic acid With pyridine; triphenyl phosphite at 150℃; for 0.166667h; microwave irradiation; Stage #2: 2-methoxyethylamine at 220℃; for 0.0666667h; microwave irradiation;	100%

BOC-glycine (4530-20-5) + anthranilic acid (118-92-3) + 2-methoxyethylamine (109-85-3) → [3-(2-methoxyethyl)-4-oxo-3,4-dihydroquinazolin-2-yl-methyl]carbamic acid tert-butyl ester

Conditions	Yield
Stage #1: BOC-glycine; anthranilic acid With pyridine; triphenyl phosphite at 150℃; for 0.166667h; microwave irradiation; Stage #2: 2-methoxyethylamine at 180℃; for 0.05h; microwave irradiation;	100%

(3S,10R,16S)-16-{(1R)-3-[4-(hydroxymethyl)phenyl]-1-methylallyl}-3-isobutyl-10-(4-methoxybenzyl)-1-oxa-4,8,11-triazacyclohexadec-13-ene-2,5,9,12-tetraone (916452-54-5) + BOC-glycine (4530-20-5) → tert-butoxycarbonylamino-acetic acid 4-{3-[3-isobutyl-10-(4-methoxy-benzyl)-2,5,9,12-tetraoxo-1-oxa-4,8,11-triaza-cyclohexadec-13-en-16-yl]-but-1-enyl}-benzyl ester (916452-55-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	100%

BOC-glycine (4530-20-5) + trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-amine → [[[(trans-7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)amino]carbonyl]methyl]carbamic acid 1,1-dimethylethyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 3h; pH=9;	100%

BOC-glycine (4530-20-5) → 2-(N-t-butoxycarbonylamino)thioacetamide (89226-13-1)

Conditions	Yield
With Lawessons reagent In dichloromethane at 25℃; for 16h;	100%
Stage #1: BOC-glycine With ammonium hydroxide; triethylamine; isobutyl chloroformate In tetrahydrofuran Stage #2: With tetraphosphorus decasulfide; sodium carbonate In tetrahydrofuran	83%
Multi-step reaction with 3 steps 1: Et3N / tetrahydrofuran / 0.42 h / -10 °C 2: aq. MH3 / tetrahydrofuran / 0.75 h / -10 °C 3: 85 percent / Lawesson's reagent / CH2Cl2 / 16 h / Ambient temperature View Scheme

BOC-glycine (4530-20-5) + p-aminoiodobenzene (540-37-4) → [(4-iodophenylcarbamoyl)methyl]carbamic acid tert-butyl ester (216774-64-0)

Conditions	Yield
With dacarbazine; dmap In dichloromethane	100%
With dmap; diisopropyl-carbodiimide In dichloromethane for 20h; Inert atmosphere;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h;	98%

BOC-glycine (4530-20-5) + bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride (68641-49-6) → (R*)-N-[[2-[N-[(1,1-Dimethylethoxy)carbonyl]glycyl]-1,2,3,4-tetrahydro-3-isoquinolinyl]carbonyl]-L-methionine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	100%

BOC-glycine (4530-20-5) + N,N-didodecylamine (3007-31-6) → C31H62N2O3 (879004-97-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h;	100%

Upstream product

• 24608-52-4 tert-butyl chloroformate 
• 56-40-6 glycine 
• 3392-07-2 tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate 
• 79113-14-7 4-nitrobenzyl N-(tert-butoxycarbonyl)glycinate 
• 50903-47-4 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 
• 17693-18-4 Boc-Gly-OPCP 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 83316-95-4 2-oxo-2-phenylethyl 2-(tert-butoxycarbonylamino)acetate 
• 120157-94-0 N-(tert-butoxycarbonyl)p-methoxybenzylamine 
• 618068-89-6 N-Boc-glycine 2-(2-acetylphenyl)-1-methylethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 1262723-01-2 tert-butyl (((2-oxo-2-(pyren-3-yl)ethoxy)carbonyl)methyl)carbamate 
• 1473417-55-8 Boc-Gly-OAcm 

Downstream Products

• 3392-14-1 N-tert-butoxycarbonyl-glycyl=>phenylalanyl=>glycine ethyl ester; N-tert-butoxycarbonyl-glycyl=>L-phenylalanyl=>glycine ethyl ester 
• 721-66-4 glycylphenylalanine 
• 57735-92-9 Boc-Gly-ODNP 
• 3655-05-8 tert-butoxycarbonylglycine p-nitrophenylester 
• 34573-36-9 N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester 
• 51779-74-9 Boc-Gly 4-Nitroguajakolester 
• 50903-47-4 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 
• 46742-14-7 glycine-(N'-benzyloxycarbonyl-hydrazide) 
• 3885-05-0 N-t-butyloxycarbonyl-glycyl-L-tyrosine-hydrazide 
• 98905-94-3 tert.Butyloxycarbonyl-glycyl-glykolyl-glycin-<4-nitro-benzylester> 
• 17790-86-2 tert-butyl 2-oxo-2-(2-phenylhydrazinyl)ethylcarbamate 
• 16561-91-4 N-tert-butoxycarbonyl-glycine 3-oxo-2-trityl-isoxazolidin-4-ylamide 
• 67706-68-7 ethyl 4-<(tert-butoxycarbonyl)amino>-3-oxobutanoate 
• 108985-35-9 Boc-Gly-Glc-OBn 

Relevant articles and documents

Discovery of degradable niclosamide derivatives able to specially inhibit small cell lung cancer (SCLC)

Small cell lung cancer (SCLC) is exceedingly tough to treat and easy to develop resistance upon long use of the first-line drug carboplatin or radiotherapy. Novel medicines effective and specific against SCLC are greatly needed. Herein, we focused on the discovery of such a medicine by exploring a drug niclosamide with repurposing strategy. Initial screening efforts revealed that niclosamide, an anthelmintic drug, possessed the in vitro anticancer activity and an obvious sensitivity towards SCLC. This observation inspired the evaluation for two different kinds of niclosamide derivatives. 2 with a degradable ester as a linker exhibited the comparable activity but slightly inferior selectivity to SCLC, by contrast, the cytotoxicities of 4 and 5 with non-degradable ether linkages completely disappeared, clearly validating the importance of 2-free hydroxyl group or 2-hydroxyl group released in the antitumor activity. Mechanism study unfolded that, similar to niclosamide, 2 inhibited growth of cancer cells via p 53 activation and subsequent underwent cytochrome c dependent apoptosis. Further structural modification to afford phosphate sodium 8 with significantly enhanced aqueous solubility (22.1 mg/mL) and a good selectivity towards SCLC demonstrated more promising druggability profiles. Accordingly, niclosamide as an attractive lead hold a huge potential for developing targeted anti-SCLC drugs.

PHOTOLYTIC COMPOUNDS AND TRIPLET-TRIPLET ANNIHILATION MEDIATED PHOTOLYSIS

The invention provides novel photolytic compounds and prodrugs, nanoparticles and compositions thereof, and methods of conducting photolysis mediated by triplet-triplet annihilation.

Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber's congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin molecules, which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chemical chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analogue 11-cis-6mr-retinal. Following molecular docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new molecules displayed an effect in at least one assay, acting either as chemical chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.