Triphosgene → HCID 57078930, compound

HRID 1279122Notes

Reaction equation

HRID 1279122 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

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 6344DichloromethaneSolvent2×

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 removeed 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

Sources & evidence

ORD record
ord-285978819c37462595b7d2605421b80b
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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