Glycine, N-acetyl-N-phenyl- → (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

HRID 374265

Reaction equation

HRID 374265 reaction equation
[OH:1][CH2:2][CH:3]1[CH:6]([CH2:7][OH:8])[CH2:5][CH:4]1[NH2:9].[CH3:10][C:11]([N:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:12]>CO>[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[CH2:5][C@H:4]1[NH2:9].[CH3:10][C:11]([N:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][C:15]([OH:17])=[O:16])=[O:12]

Participants

4

Reactant 2

HCID 68483Glycine, N-acetyl-N-phenyl-HCID 197942472,3-Bis(hydroxymethyl)-1-cyclobutylamine

Product 1

HCID 131717654(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

913 mg of (1RS, 2RS, 3SR)-2,3-bis(hydroxymethyl)-1-cyclobutylamine was dissolved in 30 ml of methanol. Then 1340 mg of N-acetyl-L-phenylglycine was added thereto to form salt. The reaction mixture was concentrated under reduced pressure. 15 ml of isopropyl alcohol was added to the residue followed by fractional recrystallization. Thus 403.8 mg of (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine/N-acetyl-L-phenylglycine salt was obtained.

Workup

  1. customto form salt
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. addition15 ml of isopropyl alcohol was added to the residue
  4. customfollowed by fractional recrystallization

Sources & evidence

ORD record
ord-f8c228103fd845eda2655b4240e94594
Source dataset
uspto-grants-1992_11
Patent number
US05166397

Linked notes

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