Methyl chloroformate → HCID 71711233, compound

HRID 2403203Notes

Reaction equation

HRID 2403203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:27]([NH:29][C:30]2([C:33]#[N:34])[CH2:32][CH2:31]2)=[O:28])[CH2:12]1)(=[O:10])=[O:9].Cl[C:36]([O:38][CH3:39])=[O:37]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([N:21]3[CH2:22][CH2:23][N:24]([C:36]([O:38][CH3:39])=[O:37])[CH2:25][CH2:26]3)[CH2:19][CH2:20]2)=[O:17])[C@H:13]([C:27](=[O:28])[NH:29][C:30]2([C:33]#[N:34])[CH2:31][CH2:32]2)[CH2:12]1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 6586Methyl chloroformateHCID 71711171HCID 71711171, compound

Product 1

HCID 71711233HCID 71711233, compoundYield 81%

Procedure

To a solution of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(piperazin-1-yl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide (35.4 mg, 70 μmol) in methylenehloride (0.7 mL) was added under stirring ethyldiisopropyl amine (18.3 μL, 105 μmol) and methyl chloroformate (6.15 μL, 77.0 μmol). The reaction was stirred at room temperature over night. The reaction was purified by column chromatography on silica gel using a gradient from methylenechloride to a mixture of methylenechloride/methanol (v:v 19:1) as solvent to yield the title compound as a white solid (32 mg, 80%). MS ISP (m/e): 564.3/566.1 (100/40) [(M+H)]+.

Workup

  1. customThe reaction was purified by column chromatography on silica gel using a gradient from methylenechloride
  2. additionto a mixture of methylenechloride/methanol (v:v 19:1) as solvent

Sources & evidence

ORD record
ord-6a62443998dc47928b5277b05825b13a
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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