Water → HCID 22276979, compound

HRID 1063928Notes

Reaction equation

HRID 1063928 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:40])[CH2:10][C:11]1([C:28]2[S:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=3)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1.[CH2:41]([N:43]=[C:44]=[O:45])[CH3:42].O>ClCCl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:40])[CH2:10][C:11]1([C:28]2[S:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:44]([NH:43][CH2:41][CH3:42])=[O:45])[CH:34]=3)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 22276469HCID 22276469, compound

Product 1

HCID 22276979HCID 22276979, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-tetrahydropyranyloxy)-2-[7-(5-(3-aminophenyl)-2-thienyl)-4-benzoyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (150 mg) in dichloromethane (3 ml) was added ethyl isocyanate (22 mg) at 0° C. and the reaction mixture was stirred at ambient temperature for 5 hours. The mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel 60 (3% methanol-chloroform) to give N-(2-tetrahydropyranyloxy)-2-[4-benzoyl-7-(5-(3-(ethylaminocarbonylamino)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (75 mg) as a white powder.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel 60 (3% methanol-chloroform)

Sources & evidence

ORD record
ord-f1dca7dfaacc49d69b9b887b4ebca895
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

Loading…