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

HRID 1167674
Notes
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Reaction equation

HRID 1167674 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 24386Thionyl ChlorideHCID 137568233-amino-(2S)-benzyloxycarbonylamino propionic acid hydrochloride

Product 1

HCID 13756825Methyl 2-(S)-[N-carbobenzyloxy]amino-3-aminopropionate, hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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

  1. filtrationthe precipitate is filtered off with suction
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes