(3-Chlorophenyl)methanesulfonyl chloride → 3-(3-Chlorobenzylsulfonyl)amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 413453Notes

Reaction equation

HRID 413453 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][S:6](Cl)(=[O:8])=[O:7].[NH2:13][C:14]1[C:15](=[O:29])[N:16]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([CH3:20])=[CH:18][CH:19]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][S:6]([NH:13][C:14]1[C:15](=[O:29])[N:16]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([CH3:20])=[CH:18][CH:19]=1)(=[O:8])=[O:7]

Participants

3

Reactant 2

HCID 2757802(3-Chlorophenyl)methanesulfonyl chlorideHCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 221786563-(3-Chlorobenzylsulfonyl)amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Procedure

The title compound was prepared from 3-chlorobenzylsulfonyl chloride (113 mg, 0.5 mmol), as prepared in the preceding step, and 3-amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (120 mg, 0.5 mmol), as prepared in step 3 of Example 1, using the procedure in step 4 of Example 1, as a white solid (180 mg, 84%). 1H-NMR (300 MHz, CDCl3) δ7.37 (d, J=7.6 Hz, 1H), 7.30 (m, 4H), 7.20 (s, 1H), 6.02 (d, J=7.7 Hz, 1H), 4.78 (s, 2H), 4.27 (s, 2H), 2.27 (s, 3H), 1.50 (s, 9H).

Workup

  1. customas prepared in step 3 of Example 1

Sources & evidence

ORD record
ord-16ff35ad69d04b26b0f29e4e9a87c4ad
Source dataset
uspto-grants-2003_05
Patent number
US06566379B1

Reaction notes

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