Formic Acid → 4-[Bis(2-chloroethyl)amino]-N-formyl-L-phenylalanine

HRID 1463541Notes

Reaction equation

HRID 1463541 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1.[CH:20](O)=[O:21]>C(OC(=O)C)(=O)C>[CH:20]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N:4]([CH2:17][CH2:18][Cl:19])[CH2:3][CH2:2][Cl:1])=[CH:16][CH:15]=1)=[O:21]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 460612Melphalan

Product 1

HCID 236204244-[Bis(2-chloroethyl)amino]-N-formyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 4-[bis(2-chloroethyl)amino]-(L)-phenylalanine (150 mg) in formic acid (1.82 ml) and acetic anhydride (0.64 ml) is stirred at room temperature for 3 hours. The reaction mixture is concentrated to reduced volume under reduced pressure and partitioned between water (3 ml) and ethyl acetate (2×50 ml). The organic phase is dried over sodium sulphate and the solvent is evaporated under vacuum, to give N-formyl-4-[bis(2-chloroethyl)amino]-(L)-phenylalanine (160 mg) as a yellow foam, [α]D =+67° (C=2, ethanol).

Workup

  1. concentrationThe reaction mixture is concentrated to reduced volume under reduced pressure
  2. custompartitioned between water (3 ml) and ethyl acetate (2×50 ml)
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-37ad6fc867e94e77a54dd38ae17d1f9c
Source dataset
uspto-grants-1994_04
Patent number
US05300671

Reaction notes

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