{3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester → tert-Butyl 1-(3-aminophenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamate

HRID 221409Notes

Reaction equation

HRID 221409 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([N:27]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:29][O:30][CH3:31])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:12]=1)C1C=CC=CC=1>Cl>[NH2:10][C:11]1[CH:12]=[C:13]([CH:17]([N:27]([CH2:28][CH2:29][O:30][CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 67329507{3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester

Product 1

HCID 58378837tert-Butyl 1-(3-aminophenyl)-2-(tert-butyldimethylsilyloxy)ethyl(2-methoxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

{3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester was added to ethanolic HCl (20 mL) at 0° C., allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated to give the title compound as a light yellow oil (300 mg).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d101d3fdc9f9422e883fa73150dc9dd6
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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