Methanol → Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochloride

HRID 36646Notes

Reaction equation

HRID 36646 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH2:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O.[CH3:22]O>>[ClH:20].[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][NH2:17])[C:13]([O:15][CH3:22])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2756313Z-Dap-OH

Product 1

HCID 13756825Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochloride

Procedure

To a cooled suspension of 2(S)-benzyloxycarbonylamino-3-aminopropionic acid (Fluka) (23-1) (10 g, 0.042 mol) in 150 ml of methanol was added 5.47 g (0.046 mol) of thionyl chloride over 20 minutes. The resulting solution was allowed to stir at room temperature overnight. After ~18 hrs, the solvent was removed in vacuo, and the residual solid was stirred with 150 ml of ether for 0.5 hr. The resulting white solid was collected and air dried to give 23-2.

Workup

  1. waitAfter ~18 hrs
  2. customthe solvent was removed in vacuo
  3. stirringthe residual solid was stirred with 150 ml of ether for 0.5 hr
  4. customThe resulting white solid was collected
  5. customair dried
  6. customto give 23-2

Sources & evidence

ORD record
ord-ba3be51385334037bc72eba61e43c030
Source dataset
uspto-grants-1995_05
Patent number
US05416099

Reaction notes

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