Diisopropylethylamine → HCID 59543518, compound

HRID 1697513Notes

Reaction equation

HRID 1697513 reaction equation
Cl.[C:2]([CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][C@@H:11]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])(=[O:15])=[O:14])[CH2:10][NH:9]1)=[O:7])#[N:3].C(N(C(C)C)CC)(C)C.Cl[C:36]([O:38][CH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1)=[O:37]>C(#N)C>[CH:39]1([O:38][C:36]([N:9]2[CH2:10][C@H:11]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:23])[F:24])(=[O:15])=[O:14])[CH2:12][C@H:8]2[C:6](=[O:7])[NH:5][CH2:4][C:2]#[N:3])=[O:37])[CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735892Cyclopentyl chloroformateHCID 86646815HCID 86646815, compound

Product 1

HCID 59543518HCID 59543518, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

L21. To a suspension of (2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid cyanomethyl-amide hydrochloride (0.13 mmole) from experiment K2 in acetonitrile (1 ml) was added at 22° C. diisopropyl ethyl amine (0.40 mmole) and cyclopentyl chloroformate (0.15 mmole) and stirring was continued for 2 h. The mixture was quenched with methanol, acidified with acetic acid and subjected to prep. HPLC (RP-18) using a mixture of acetonitrile and water to give (2S,4R)-2-(cyanomethyl-carbamoyl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-1-carboxylic acid cyclopentyl ester as a colorless oil. MS: 474.1 [M+H]+.

Workup

  1. customThe mixture was quenched with methanol
  2. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-31dcb0ac09fd48658211a2db047bbced
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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