Acetic Anhydride → L-Phenylalanine, methyl ester

HRID 1060410Notes

Reaction equation

HRID 1060410 reaction equation
OC(C(F)(F)F)=O.[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][C:27](C2C=CC=CC=2N)=[CH:26][CH:25]=1)[NH:12]C(=O)C1C(Cl)=CC=CC=1Cl.CC(OC(C)=O)=O.CCN(C(C)C)C(C)C.CCOC(C)=O>C1COCC1>[CH3:8][O:9][C:10](=[O:37])[C@H:11]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH2:12]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 131723775N-(2,6-dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2,6-Dichlorobenzoyl)-4-(2-aminophenyl)-L-phenylalanine methyl ester TFA salt (90 mg) was dissolved in dry THF (5 mL). Ac2O (60 μL) and DIEA (160 μL) were added and the mixture was stirred at room temperature for 12 h. EtOAc was added and the resulting mixture was extracted with water. The organic phase was dried (MgSO4) and evaporated to give N-(2,6-dichlorobenzoyl)-4-[2-(acetylamino)]phenyl]-L-phenylalanine methyl ester.

Workup

  1. extractionthe resulting mixture was extracted with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-aaee48eb7aae492995067ea1e4940b70
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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