Water → N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH)

HRID 1655294Notes

Reaction equation

HRID 1655294 reaction equation
C[O:2][C:3](=[O:26])[CH:4]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.CCOCC.O>[OH-].[Na+]>[C:22]([O:21][C:19]([NH:18][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[C:3]([OH:26])=[O:2])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 2736832Methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoate

Product 1

HCID 2761796N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH)

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(S)-2-(t-butoxycarbonylamino-3-(biphenyl-4-yl)-propionic acid methyl ester (4.1 g, 11.5 mmol) is dissolved at room temperature in methanolic 1N sodium hydroxide (60 mL). The solution is stirred for 3 hours. Ether (30 mL) and water (30 mL) are added. The aqueous layer is separated and acidified with concentrated hydrochloric acid, then extracted with ether (2×20 mL) and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gives (S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid as a white solid, m.p. 122°-123°.

Workup

  1. customThe aqueous layer is separated
  2. extractionextracted with ether (2×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-db66ccf862ca4008bdc7f35329cba1e5
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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