2,2,2-Trichloro-n-methylacetamide → (+)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

HRID 2394476Notes

Reaction equation

HRID 2394476 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([CH:27]=1)[C:7]([NH:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([S:21](=[O:24])(=[O:23])[NH2:22])[CH:19]=2)[O:14][CH2:13][CH2:12]1)=[O:8].[CH3:30][NH:31][C:32](=[O:37])C(Cl)(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([CH:27]=1)[C:7]([NH:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([S:21]([NH:22][C:32]([NH:31][CH3:30])=[O:37])(=[O:23])=[O:24])[CH:19]=2)[O:14][CH2:13][CH2:12]1)=[O:8]

Participants

4

Reactant 2

HCID 2486522,2,2-Trichloro-n-methylacetamideHCID 110484644-(5-Chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman

Product 1

HCID 11755624(+)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(-)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman ##STR60## (-)-4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminocarbonyl-aminosulfonyl)-7-methoxychroman is prepared analogously to Example 1 from optically active 4-(5-chloro-2-methoxybenzamido methyl)-6-sulfamoyl-7-methoxychroman and N-methyltrichloroacetamide. Melting point: 239° C.; [α]D20 : -59.8° (c=1, DMF); HPLC: ee 98.5%.

Sources & evidence

ORD record
ord-a0866739151544709e86a8258e55171e
Source dataset
uspto-grants-1998_09
Patent number
US05811448

Reaction notes

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