Benzenesulfonyl chloride → HCID 86679525, compound

HRID 1776569Notes

Reaction equation

HRID 1776569 reaction equation
[C:1]([S:4][C:5]([CH3:38])([CH3:37])[CH:6]([NH2:36])[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:17]([Cl:18])=[CH:16][N+:15]([O-:19])=[CH:14][C:13]=1[Cl:20])=[O:8])(=[O:3])[CH3:2].[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>N1C=CC=CC=1>[C:1]([S:4][C:5]([CH3:38])([CH3:37])[CH:6]([NH:36][S:45]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:47])=[O:46])[C:7]([O:9][C@H:10]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[C:23]([O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:22]=1)[CH2:11][C:12]1[C:13]([Cl:20])=[CH:14][N+:15]([O-:19])=[CH:16][C:17]=1[Cl:18])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 86679524HCID 86679524, compound

Product 1

HCID 86679525HCID 86679525, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-((2S)-2-(3-(acetylthio)-2-amino-3-methylbutanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (101 mg, 0.170 mmol) was dissolved in pyridine (1 ml), then benzenesulfonyl chloride (60 mg, 0.340 mmol) was added at 0° C., and the mixture was stirred at RT for 2 hours. The reaction was quenched with HCl 1N, and the product was extracted with EtOAc. The organic phase was washed with HCl 1N (2×) and brine, then dried over Na2SO4. The solvent was removed and the crude product was purified by preparative reverse-phase HPLC to give 10 mg of the desired compound (Yield 8%).

Workup

  1. customThe reaction was quenched with HCl 1N
  2. extractionthe product was extracted with EtOAc
  3. washThe organic phase was washed with HCl 1N (2×) and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-6f3552902597445382ea767e7e0bf049
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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