Methanesulfonyl chloride → HCID 71542916, compound

HRID 1776614Notes

Reaction equation

HRID 1776614 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([O:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:36][CH:35]=1)[C:4]([O:6][C@H:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][N+:12]([O-:16])=[CH:11][C:10]=1[Cl:17])=[O:5].[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(Cl)Cl.N1C=CC=CC=1>[Cl:15][C:14]1[CH:13]=[N+:12]([O-:16])[CH:11]=[C:10]([Cl:17])[C:9]=1[CH2:8][C@@H:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[O:6][C:4](=[O:5])[C@@H:3]([NH:2][S:46]([CH3:45])(=[O:48])=[O:47])[CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:40][S:41]([CH3:44])(=[O:42])=[O:43])=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86719337HCID 86719337, compound

Product 1

HCID 71542916HCID 71542916, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-((S)-2-((S)-2-amino-3-(4-(methylsulfonyloxy)phenyl)propanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide hydrochloride (30 mg, 0.05 mmol) was dissolved in DCM (2 ml) and pyridine (100 μl), then methanesulfonyl chloride (7 mg, 0.06 mmol) was added. The mixture was stirred at RT for 2 h, then was washed with HCl 1N (2×). The crude was purified by semi-preparative HPLC to give 29 mg of the final compound (Yield: 80%)

Workup

  1. washwas washed with HCl 1N (2×)
  2. customThe crude was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-a848d1008714405ebb47fe24920b874f
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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