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Boc-3-Hydroxy-1-adamantyl-D-glycine
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Name

Boc-3-Hydroxy-1-adamantyl-D-glycine

 EINECS 700-361-0
CAS No. 361442-00-4 Density 1.296 g/cm3
PSA 95.86000 LogP 2.68650
Solubility N/A Melting Point N/A
Formula C17H27NO5 Boiling Point 497.253 °C at 760 mmHg
Molecular Weight 325.405 Flash Point 254.53 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 361442-00-4 (Boc-3-Hydroxy-1-adamantyl-D-glycine) Hazard Symbols N/A
Synonyms

(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid;Tricyclo[3.3.1.13,7]decane-1-acetic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-, (aS)-;

Article Data 16

Boc-3-Hydroxy-1-adamantyl-D-glycine Synthetic route

N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine ethyl ester

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 18 - 65℃; for 2h;98.1%

(αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

24424-99-5

di-tert-butyl dicarbonate

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 12h;98%
With potassium phosphate In tetrahydrofuran; sodium hydroxide at 20℃; for 2h;88%
Stage #1: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate With sodium hydroxide for 4h; pH=10;
Stage #2: With sulfuric acid In Isopropyl acetate; water for 0.0833333 - 0.166667h; pH=2.0 - 8;		88%

N-tert-butoxycarbonyl-3-hydroxy-1-adamantaneglycine

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With (1R,2S)-2-Amino-1,2-diphenylethanol In ethyl acetate at 20℃; for 2h; Reflux; Resolution of racemate;56%
Multi-step reaction with 2 steps
1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate
2: hydrogenchloride / ethyl acetate; water / pH 3
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 0.08 h / Resolution of racemate; Reflux
2: hydrogenchloride / water; ethyl acetate / pH 2
View Scheme
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

A

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

B

681282-72-4

(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate at 60 - 90℃; for 1.5h;A 51%
B 17%
With potassium hydroxide; potassium permanganate In water at 60 - 90℃; for 1.5h;A 51%
B 17%
361441-97-6

(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
With potassium permanganate; water; potassium hydroxide at 60 - 90℃; for 1.5h;51%
With potassium permanganate; potassium hydroxide at 90℃;49%
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 25℃;18.6 g
361441-95-4

(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
3: 4.07 g / K2CO3 / dimethylformamide / 19 h
4: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 80 °C
2: hydrogen; palladium 10% on activated carbon / acetic acid
3: triethylamine / methanol
4: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
4: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme

(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
2: 4.07 g / K2CO3 / dimethylformamide / 19 h
3: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / acetic acid
2: triethylamine / methanol
3: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 3 steps
1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
2.2: 0 - 5 °C
3.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
3: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
770-71-8

1-adamantanemethanol

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
5: 4.07 g / K2CO3 / dimethylformamide / 19 h
6: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
1.2: 0 - 5 °C
2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
5.2: 0 - 5 °C
6.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 6 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
6.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium bromide / dichloromethane; water / 12 h / 5 - 30 °C
2.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
3.1: sulfuric acid / 45 - 50 °C
3.2: 2 h / 20 - 35 °C
4.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
5.1: sulfuric acid / 110 - 112 °C
6.1: sulfuric acid; nitric acid / 10 - 25 °C
7.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme
828-51-3

1-Adamantanecarboxylic acid

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C
2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C
3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
7: 4.07 g / K2CO3 / dimethylformamide / 19 h
8: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 3 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C
3.2: 0 - 5 °C
4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
7.2: 0 - 5 °C
8.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 8 steps
1.1: thionyl chloride / 4 h / Reflux
2.1: sodium / Petroleum ether / 20 °C
2.2: 20 °C
2.3: 6 h / Reflux
3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C
4.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h
5.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C
6.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10
7.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C
8.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate
View Scheme
2094-74-8

1-Adamantanecarbaldehyde

361442-00-4

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating
2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C
3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr
4: 4.07 g / K2CO3 / dimethylformamide / 19 h
5: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / 0 - 60 °C
2: hydrogenchloride; water / acetic acid / 80 °C
3: hydrogen; palladium 10% on activated carbon / acetic acid
4: triethylamine / methanol
5: potassium permanganate; potassium hydroxide / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C
2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C
3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C
4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C
4.2: 0 - 5 °C
5.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C
View Scheme
Multi-step reaction with 5 steps
1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux
2: hydrogenchloride; water / acetic acid / 18 h / 80 °C
3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr
4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
5: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C
2.1: sulfuric acid / 45 - 50 °C
2.2: 2 h / 20 - 35 °C
3.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr
4.1: sulfuric acid / 110 - 112 °C
5.1: sulfuric acid; nitric acid / 10 - 25 °C
6.1: sodium hydroxide / 5 h / 25 - 30 °C
View Scheme

Boc-3-Hydroxy-1-adamantyl-D-glycine Specification

The CAS registry number of Boc-3-Hydroxy-1-adamantyl-D-glycine is 361442-00-4. The IUPAC name is (2S)-[(tert-butoxycarbonyl)amino](3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)ethanoic acid. In addition, the formula is C17H27NO5 and the molecular weight is 325.4.

Physical properties about Boc-3-Hydroxy-1-adamantyl-D-glycine are: (1)ACD/LogP: 1.97; (2)# of Rule of 5 Violations: 0 ; (3)#H bond acceptors: 6; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 6; (6)Polar Surface Area: 95.86 Å2; (7)Index of Refraction: 1.575; (8)Molar Refractivity: 82.911 cm3; (9)Molar Volume: 251.06 cm3; (10)Polarizability: 32.868 ×10-24cm3; (11)Surface Tension: 59.817 dyne/cm; (12)Density: 1.296 g/cm3; (13)Flash Point: 254.53 °C; (14)Enthalpy of Vaporization: 88.13 kJ/mol; (15)Boiling Point: 497.253 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)N[C@H](C(=O)O)C12CC3CC(O)(C1)CC(C2)C3
(2)InChI: InChI=1/C17H27NO5/c1-15(2,3)23-14(21)18-12(13(19)20)16-5-10-4-11(6-16)8-17(22,7-10)9-16/h10-12,22H,4-9H2,1-3H3,(H,18,21)(H,19,20)/t10?,11?,12-,16?,17?/m1/s1
(3)InChIKey: UKCKDSNFBFHSHC-ZEJPWUNMBX

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