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

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].S(Cl)([Cl:20])=O.[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

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2756313Z-Dap-OH

Product 1

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

Procedure

To the compound obtained in Step 1 were added methanol (100 ml) and thionyl chloride (2.4 ml), and the mixture was stirred overnight at room temperature. The solvent was evaporated to give the title compound as a crude product.

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-8a8273912e574903ba20d785b22b3f70
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728005B2

Reaction notes

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