Ammonia → Carbamic acid, [(1S)-3-amino-3-oxo-1-phenylpropyl]-, 1,1-dimethylethyl ester

HRID 895296Notes

Reaction equation

HRID 895296 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:24]([O:28][C:29]([NH:31][C@H:32]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:33][C:34](O)=[O:35])=[O:30])([CH3:27])([CH3:26])[CH3:25].N>ClCCl>[NH2:3][C:34](=[O:35])[CH2:33][C@H:32]([NH:31][C:29](=[O:30])[O:28][C:24]([CH3:27])([CH3:26])[CH3:25])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734490(3S)-3-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 60017220Carbamic acid, [(1S)-3-amino-3-oxo-1-phenylpropyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-hydroxybenzotriazole hydrate (3.46 g, 25.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.91 g, 25.6 mmol), and (S)-N-tert-butoxycarbonyl-3-amino-3-phenylpropanoic acid (6.80 g, 25.6 mmol) in dichloromethane (250 ml) was stirred at room temperature for 1 hour. 0.88 Ammonia (20 ml) was added and the mixture stirred at room temperature for a further 18 hours. The resulting solid was filtered off and washed with sodium bicarbonate solution, then water and dried under vacuum at 50° C. to afford the title compound, 6.78 g.

Workup

  1. stirringthe mixture stirred at room temperature for a further 18 hours
  2. filtrationThe resulting solid was filtered off
  3. washwashed with sodium bicarbonate solution
  4. dry with materialwater and dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-728c27ccd55248bbaad391bf9e33bd21
Source dataset
uspto-grants-2005_07
Patent number
US06914160B1

Reaction notes

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