Methanesulfonyl chloride → (2R,3R,4S)-6-methanesulfonylamino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

HRID 29036Notes

Reaction equation

HRID 29036 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([OH:17])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[O:20][C:19]3=[S:27])[C:6]=2[CH:28]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C@:9]([CH:12]([O:15][CH3:16])[O:13][CH3:14])([CH3:11])[C@H:8]([OH:17])[C@@H:7]([N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[O:20][C:19]3=[S:27])[C:6]=2[CH:28]=1)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86612091(2R,3R,4S)-6-amino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyran

Product 1

HCID 86612096(2R,3R,4S)-6-methanesulfonylamino-3,4-dihydro-3-hydroxy-2-dimethoxymethyl-2-methyl-4-(2-thioxobenzoxazol-3-yl)-2H-1-benzopyranYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

90 mg (0.22 mmol) of the compound prepared in Example 17 was dissolved in 1 ml of dichloromethane, to which 58 μl (0.34 mmol) of methanesulfonyl chloride and 17 μl (0.22 mmol) of diaisopropylethylamine were added. The reaction was stirred for 10 hours at room temperature, 67 mg (yield: 64%) of the target compound was obtained through reaction accomplished by the same procedure as used in Example 33.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-8116e3d95a0e44f68ac2555350968c2d
Source dataset
uspto-grants-2008_09
Patent number
US07420060B2

Reaction notes

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