Diisopropylethylamine → HCID 59543674, compound

HRID 1697527Notes

Reaction equation

HRID 1697527 reaction equation
Cl.[C:2]([C:4]1([NH:7][C:8]([C@@H:10]2[CH2:14][C@@H:13]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])(=[O:17])=[O:16])[CH2:12][NH:11]2)=[O:9])[CH2:6][CH2:5]1)#[N:3].C(N(C(C)C)CC)(C)C.O([CH2:42][CH:43]([F:45])[F:44])S(C(F)(F)F)(=O)=O>C1COCC1>[C:2]([C:4]1([NH:7][C:8]([C@@H:10]2[CH2:14][C@@H:13]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])(=[O:17])=[O:16])[CH2:12][N:11]2[CH2:42][CH:43]([F:45])[F:44])=[O:9])[CH2:6][CH2:5]1)#[N:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 66770259HCID 66770259, compound

Product 1

HCID 59543674HCID 59543674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (2S,4R)-4-(2-chloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide hydrochloride (0.13 mmole) from experiment K4 in THF (2 ml) was added at 22° C. diisopropyl ethyl amine (0.75 mmole) and 2,2-difluoroethyl triflate (0.60 mmole) and stirring was continued at 60° C. for 24 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)-4-(2-chloro-benzenesulfonyl)-1-(2,2-difluoro-ethyl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide as a colorless oil. MS: 418.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-cdf6b27332104a8f8d81176bf00570ff
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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