187960-74-3

Basic information

• Product Name: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID
• Synonyms: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID
• CAS NO: 187960-74-3
• Molecular Formula: C₂₁H₃₂N₂O₈
• Molecular Weight: 440.49
• Mol File: 187960-74-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 125-127 °C
• Boiling Point: 632.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• PKA: 3.87±0.10(Predicted)
• CAS DataBase Reference: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(187960-74-3)
• EPA Substance Registry System: 3,5-BIS[2-(BOC-AMINO)ETHOXY]-BENZOIC ACID(187960-74-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 187960-74-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

3,5-bis-(2-tert-butyloxycarbonylamino-ethoxy) methyl benzoate (184916-28-7) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
With sodium hydroxide	100%
With sodium hydroxide In 1,4-dioxane; methanol; water for 5h;	96%
With water; sodium hydroxide In 1,4-dioxane; methanol for 5h;	96%

di-tert-butyl dicarbonate (24424-99-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: NEt3 / CH2Cl2 / 27 h / 0 °C 2: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 3: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 0 °C 2: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 0 °C 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; potassium carbonate / acetone / 16 h / 65 °C / Inert atmosphere 2.1: sodium hydroxide / water; methanol / 2 h / 70 °C / Inert atmosphere 2.2: pH 3 / Inert atmosphere View Scheme

3,5-Dihydroxybenzoic acid (99-10-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / H2SO4 / Heating 2: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 3: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 3: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme

2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) → 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / K2CO3 / dimethylformamide / 16 h / 40 °C 2: 95 percent / Tesser's base / 4.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide / water; methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C 2: sodium hydroxide; water / methanol; 1,4-dioxane / 5 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium iodide; potassium carbonate / acetone / 16 h / 65 °C / Inert atmosphere 2.1: sodium hydroxide / water; methanol / 2 h / 70 °C / Inert atmosphere 2.2: pH 3 / Inert atmosphere View Scheme

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) + 3,5-Bis-(2-amino-ethoxy)-benzoic acid methyl ester; hydrochloride → 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid methyl ester (187960-76-5)

Conditions	Yield
With BOP-peptide	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h;	95%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-(di-aminoethoxy)-benzoic acid dihydrochloride

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane for 2h;	100%
With hydrogenchloride In diethyl ether; dichloromethane; water for 2h;	100%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → N-(benzyloxy)-3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzamide (1228435-28-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	86%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) + N-Fmoc-L-Ser(t-But)-OEt → N-Boc-L-Phe-L-Ser(t-But)-OEt

Conditions	Yield
With potassium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 5h; Substitution;	84%

C18H33NO7P2 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C39H63N3O14P2

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;	65%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	65%

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid (352426-84-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / BOP; N,N-diisopropylethylamine (DiPEA) / CH2Cl2 / 1.5 h / 20 °C 2: 94 percent / Tesser's base / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / BOP 2: NaOH View Scheme
Multi-step reaction with 2 steps 1: 100 percent / BOP-peptide 2: NaOH View Scheme

3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → 3,5-bis(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)benzoic acid (1185295-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; diethyl ether / 2 h 2: sodium carbonate / water; acetone / 18 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; water; diethyl ether / 2 h 2: sodium carbonate / water; acetone / 18 h / 20 °C View Scheme

C18H33NO7P2 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C29H47N3O10P2*2C2HF3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere View Scheme

C10H9N3O + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C31H39N5O8

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	466 mg

C21H23N5O4 + 3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzoic acid (187960-74-3) → C63H83N9O18

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;	70 mg

Upstream product

• 184916-28-7 3,5-bis-(2-tert-butyloxycarbonylamino-ethoxy) methyl benzoate 
• 39684-80-5 2-(tert-butoxycarbonylamino)ethyl bromide 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1228435-28-6 N-(benzyloxy)-3,5-bis[2-(tert-butoxycarbonylamino)ethoxy]benzamide 
• 352426-84-7 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid 
• 187960-76-5 3,5-Bis-{2-[3,5-bis-(2-tert-butoxycarbonylamino-ethoxy)-benzoylamino]-ethoxy}-benzoic acid methyl ester 
• 1185295-67-3 3,5-bis(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethoxy)benzoic acid 

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