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Formic Acid → N-formylphenylalanine methyl ester

HRID 2968
Notes
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Reaction equation

HRID 2968 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH:22](O)=[O:23].C(OC(=O)C)(=O)C>CN(C=O)C>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][CH:22]=[O:23]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 7016392N-formylphenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1 mmol of phenylalanine methyl ester hydrochloride and 2 mmol of triethylamine in 1 mL of DMF at 0 ° C. was added 2 mL of formic acid and 0.7 mL of acetic anhydride. After stirring for 16 h at rt, extractive isolation provided N-formylphenylalanine methyl ester.

Sources & evidence

ORD record
ord-2f2ad81b1f6b433ea7c984999ad32978
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731432

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes