Hydrochloric Acid → 3-{[(Benzyloxy)carbonyl]amino}-3-phenylpropanoic acid

HRID 375787Notes

Reaction equation

HRID 375787 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:12])[CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[OH-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].Cl>>[C:16]([NH:12][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH2:8][C:9]([OH:11])=[O:10])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 69189DL-beta-Phenylalanine

Product 1

HCID 3042733-{[(Benzyloxy)carbonyl]amino}-3-phenylpropanoic acidYield 83.3%

Procedure

A 0° C. slurry of 50.0 g (300 mmole) of DL-3-amino-3-phenyl propionic acid in 300 mL of 1N aq NaOH (300 mmole) was treated simultaneously with 48.0 mL (340 mmole) of benzyl chloroformate and 300 mL of 1N aq NaOH (300 mmole). The reaction was stirred at ambient temperature for 18 h at which time the reaction was acidified to pH 2 with conc. aq HCl and extracted with EtOAc (4×200 mL). The combined organic fractions were dried over Na2SO4 and evaporated in vacuo to give 73.4 g (250 mmol; 82%) of N-Cbz-3-amino-3-phenyl propionic acid as an off white solid.

Workup

  1. extractionextracted with EtOAc (4×200 mL)
  2. dry with materialThe combined organic fractions were dried over Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc72675e186a4925abf950d515cb7688
Source dataset
uspto-grants-1996_01
Patent number
US05488037

Reaction notes

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