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Triphosgene → HCID 57078930, compound

HRID 1008594
Notes
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Reaction equation

HRID 1008594 reaction equation
Cl.[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:29])[C@H:18]([NH2:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:30]([O-])(O)=[O:31].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:29])[C@H:18]([N:28]=[C:30]=[O:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 697805921-[2-(R)-Amino-3-(4-methoxyphenyl)-propionyl]-pyrrolidin-2-(S)-carboxylic acid benzyl ester hydrochloride

Product 1

HCID 57078930HCID 57078930, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Procedure

1-[2-(R)-Amino-3-(4-methoxyphenyl)-propionyl]-pyrrolidin-2-(S)-carboxylic acid benzyl ester hydrochloride (2.8 g) was dissolved in 30 mL of dichloromethane followed by addition of 30 mL of NaHCO3 solution (1M) under vigorous stirring. Triphosgene (0.6 g) in 6 mL of dichloromethane was added at 0° C. and the mixture was kept stirring for 0.25 h. The organic layer was separated and the solvent removed in vacuo to yield 1.20 g (98%) of the title compound as a yellow oil. (+)-APCI-MS: 409 (MH+).

Workup

  1. customThe organic layer was separated
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1d88d2fbd4d24b648d16884a7e2177ee
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06797710B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes