Benzyloxycarbonyl-L-phenylalanine → N-benzyloxycarbonylphenylalanine methyl ester

HRID 1617281Notes

Reaction equation

HRID 1617281 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]CN=C=NCCCN(C)C.Cl>CO.CN(C1C=CN=CC=1)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([O:12][CH3:23])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 3082435N-benzyloxycarbonylphenylalanine methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

After 1.80 g of Z-Phe was dissolved in 20 mL of MeOH, 73 mg of DMAP, 1.38 g of WSCD HCl were added at 0° C., followed by stirring at 4° C. for 12 hours. The solvent was concentrated and the concentrate was dissolved in AcOEt, followed by washing with 1N HCl aq., satd. NaHCO3 aq., and satd. NaCl aq. After drying over Na2SO4, the solvent was concentrated to give Z-Phe-OMe as oil. After dissolving in 20 mL of dry THF, 196 mg of LiBH4 was added thereto and the mixture was stirred at room temperature for 15 hours. The solvent was concentrated and the concentrate was dissolved in AcOEt and the residue was washed with 1N HCl aq., satd. NaHCO3 aq., and satd. NaCl aq. After drying over Na2SO4, the solvent was concentrated and ether-petroleum ether was added to give 1.45 g (yield 85%) of Z-Phe-ol as precipitates. After 60 mg of 60% NaH was suspended in 10 mL of dry THF, 285 mg of Z-Phe-ol, 264 mg of 18-crown-6 and 1.48 mL of tert-butyl bromoacetate were added at 0° C. While returning to room temperature, the mixture was stirred for 15 hours.

Workup

  1. concentrationThe solvent was concentrated
  2. dissolutionthe concentrate was dissolved in AcOEt
  3. washby washing with 1N HCl aq.
  4. dry with materialNaCl aq. After drying over Na2SO4
  5. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-556b3144f25e449cb5b0e49f28da9cd0
Source dataset
uspto-grants-2014_07
Patent number
US08765909B2

Reaction notes

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