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

HRID 324593Notes

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-8c1dc0e3952649f4bead5a5ed326e7b9
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218415B1

Reaction notes

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