Triethylamine → HCID 59619303, compound

HRID 1367553Notes

Reaction equation

HRID 1367553 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25]O)=[O:8])[CH2:5][CH2:4]1)#[N:2].[F:27]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C(N(CC)CC)C>O1CCCC1>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25][F:27])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 59619202HCID 59619202, compound

Product 1

HCID 59619303HCID 59619303, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R,2R,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-hydroxymethyl-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (41 mg), perfluoro-1-butanesulfonyl fluoride (62 mg), triethylamine (62 mg) and triethylamine.trishydrofluoride salt (33 mg) in tetrahydrofuran (1 mL) was stirred 24 h at room temperature. The mixture was then adsorbed unto silica and was purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl:acetate (3:1 to 1:1 v/v) as eluant to afford the title compound (10 mg, 24%) as a colorless solid. MS (EI): 403.3 (M+H)+.

Workup

  1. customwas purified by flash chromatography on silica gel with a gradient of cyclohexane:ethyl:acetate (3:1 to 1:1 v/v) as eluant

Sources & evidence

ORD record
ord-3828b6dcffff4813afbd9c1957b2b5c3
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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