Water → HCID 22276525, compound

HRID 1063926Notes

Reaction equation

HRID 1063926 reaction equation
O1CCCCC1O[CH:8]([C:12]1([C:21]2[S:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[S:18](=[O:20])(=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:9]([NH2:11])=[O:10].N1C=CC=CC=1.[CH3:39][O:40][C:41]1[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=1[C:43](Cl)=[O:44].[OH2:50]>C(Cl)(Cl)Cl>[OH:50][NH:11][C:9](=[O:10])[CH2:8][C:12]1([C:21]2[S:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[S:18](=[O:20])(=[O:19])[CH2:17][CH2:16][N:15]([C:43](=[O:44])[C:42]2[CH:46]=[CH:47][CH:48]=[CH:49][C:41]=2[O:40][CH3:39])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 889692-Methoxybenzoyl chlorideHCID 86588739HCID 86588739, compound

Product 1

HCID 22276525HCID 22276525, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of N-(2-tetrahydropyranyloxy-2-[7-(5-(4-chlorophenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (90 mg) and pyridine (0.5 ml) in chloroform (3 ml) was added 2-methoxybenzoyl chloride (37 mg) and the mixture was stirred at ambient temperature for 3 hours. The mixture was pertitioned between water and chloroform. The organic layer was separated, washed with 5% citric acid water solution, water, saturated sodium bicarbonate solution and brine. To the reaction mixture were added 4N hydrogen chloride-ethyl acetate solution (0.5 ml), chloroform (1 ml) and methanol (1.5 ml) and the reaction mixture was stirred at ambient temperature for 30 minutes. After evaporation of solvent, the residue was purified by HPLC (0.1% trifluoroacetic acid in 20% acetonitrile-water ˜0.1% trifluoroacetic acid in 80% acetonitrile-water) to give N-hydroxy-2-[7-(5-(4-chlorophenyl)-2-thienyl)-4-(2-methoxybenzoyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (54 mg) as a pale yellow powder.

Workup

  1. customThe organic layer was separated
  2. washwashed with 5% citric acid water solution, water, saturated sodium bicarbonate solution and brine
  3. additionTo the reaction mixture were added 4N hydrogen chloride-ethyl acetate solution (0.5 ml), chloroform (1 ml) and methanol (1.5 ml)
  4. stirringthe reaction mixture was stirred at ambient temperature for 30 minutes
  5. customAfter evaporation of solvent
  6. customthe residue was purified by HPLC (0.1% trifluoroacetic acid in 20% acetonitrile-water ˜0.1% trifluoroacetic acid in 80% acetonitrile-water)

Sources & evidence

ORD record
ord-0d2daa5a34b04373b35a912865d27c31
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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