4-Trifluoromethanesulfonylamino-butyryl chloride → CID 145857667

HRID 2216135Notes

Reaction equation

HRID 2216135 reaction equation
[F:1][C:2]([F:14])([F:13])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11])(=[O:5])=[O:4].[C:15]([O:19][C:20](=[O:48])[NH:21][C:22]([C:24]1[S:25][C:26]([S:46][CH3:47])=[C:27]([S:29]([C:32]2[CH:33]=[C:34]([C:38]3[C:43]([CH3:44])=[CH:42][CH:41]=[CH:40][C:39]=3[NH2:45])[CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])[CH:28]=1)=[NH:23])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([O:19][C:20](=[O:48])[NH:21][C:22](=[NH:23])[C:24]1[S:25][C:26]([S:46][CH3:47])=[C:27]([S:29]([C:32]2[CH:33]=[C:34]([C:38]3[C:43]([CH3:44])=[CH:42][CH:41]=[CH:40][C:39]=3[NH:45][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][NH:6][S:3]([C:2]([F:14])([F:13])[F:1])(=[O:5])=[O:4])[CH:35]=[CH:36][CH:37]=2)(=[O:30])=[O:31])[CH:28]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 218861334-Trifluoromethanesulfonylamino-butyryl chlorideHCID 145857623tert-butyl N-[4-[3-(2-amino-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857667CID 145857667Yield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-trifluoromethanesulfonylamino-butyryl chloride (0.015 g, 0.058 mmol) [example 212, step b] in dichloromethane [1 mL] was added to a solution of {[4-(2′-amino-6′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.025 g, 0.049 mmol) [example 25, step c] in dichloromethane [1 mL] at room temperature with vigorous stirring for 0.5 hours. The reaction mixture was evaporated and column chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (0.020 g, 57%) as a solid. ESI-MS (m/z): Calcd. for C29H33F3N4O7S4: 734.12; found: 734.7.

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-0bbf04899e9e44bfa7b1881c6b0e330c
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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