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

HRID 1167674Notes

Reaction equation

S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][C@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:9]([OH:11])=[O:10].[CH:23](OC(C)C)(C)C>CO>[ClH:3].[NH2:6][CH2:7][C@H:8]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:9]([O:11][CH3:23])=[O:10]

Participants

Conditions

Temperature: -15 °C

Procedure

7.4 ml (100.8 mmol) of thionyl chloride are added dropwise, at −15° C., to 50 ml of absolute methanol. 12 g (50.4 mmol) of 3-amino-(2S)-benzyloxycarbonylamino propionic acid hydrochloride are added, followed by 40 ml of absolute methanol. After stirring at −15° C. for 45 min and at room temperature for 20 h, the reaction mixture is poured into diisopropyl ether and the precipitate is filtered off with suction and dried under high vacuum. 14.18 g (98%) of (3.7) are obtained as a colorless solid.

Workup

filtrationthe precipitate is filtered off with suction
customdried under high vacuum

Sources & evidence

ORD record: ord-b744bd3343674955bd7a3890b9c764ac
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620820B2

Reaction notes

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