Hydrochloric Acid → (S)-benzyl 2-amino-3-(biphenyl-4-yl)propanoate hydrochloride

HRID 1655296Notes

Reaction equation

HRID 1655296 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[C@@H:10]([NH:24]C(OC(C)(C)C)=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].CCOCC>C(OCC)(=O)C>[ClH:33].[CH2:1]([O:8][C:9](=[O:32])[C@@H:10]([NH2:24])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10288035(S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid benzyl ester

Product 1

HCID 68805074(S)-benzyl 2-amino-3-(biphenyl-4-yl)propanoate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of (S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid benzyl ester (3.95 g, 9.15 mmol) in ethyl acetate (40 mL) under nitrogen is cooled to 0° and treated with hydrochloric acid gas (4 g). A precipitate appears and the mixture is warmed to room temperature and stirred for 1 hour. Ether (25 mL) is added and the solid is filtered off and briefly dried under high vacuum for 1 hour. (S)-2-amino-3-(biphenyl-4-yl)-propionic acid benzyl ester hydrochloride is obtained as white solid, [α]D =-21.14 (c 0.92, MeOH).

Workup

  1. filtrationthe solid is filtered off
  2. custombriefly dried under high vacuum for 1 hour

Sources & evidence

ORD record
ord-e3c6804795474b77a91d12186e14b262
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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