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

HRID 265866Notes

Reaction equation

HRID 265866 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([OH:6])=[O:5].O=S(Cl)[Cl:20].[CH3:22]O>>[ClH:20].[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C:4]([O:6][CH3:22])=[O:5]

Participants

4

Reactant 3

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

Product 1

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

Procedure

3-Amino-2(S)-benzyloxycarbonylaminopropionic acid (Fluka) (5.0 g, 21.0 mmoles) was suspended in MeOH and at -10° SOCl2 (23.0 mmoles) was added. The reaction mixture was allowed to gradually warm to room temperature over 16 hours. The solvent was then removed and the resulting solid was triturated with Et2O to give 10-10.

Workup

  1. additionwas added
  2. customThe solvent was then removed
  3. customthe resulting solid was triturated with Et2O
  4. customto give 10-10

Sources & evidence

ORD record
ord-5a924f8037854292836f3242c3d9f59d
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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