Isopropyl isocyanate → HCID 22276851, compound

HRID 1063927Notes

Reaction equation

HRID 1063927 reaction equation
O1CCCCC1[O:7][NH:8][C:9](=[O:33])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH:34]([N:37]=[C:38]=[O:39])([CH3:36])[CH3:35]>C(Cl)(Cl)Cl>[OH:7][NH:8][C:9](=[O:33])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][N:14]([C:38](=[O:39])[NH:37][CH:34]([CH3:36])[CH3:35])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 22276494HCID 22276494, compound

Product 1

HCID 22276851HCID 22276851, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-ethylphenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (80 mg) in chloroform (3 ml) was added isopropyl isocyanate (16.6 mg) and the mixture was stirred at ambient temperature for 3 hours. The mixture was partitioned 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-ethylphenyl)-2-thienyl)-4-isopropylcarbamoyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (36 mg) as a pale yellow powder.

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. customThe organic layer was separated
  3. washwashed with 5% citric acid water solution, water, saturated sodium bicarbonate solution and brine
  4. additionTo the reaction mixture were added 4N hydrogen chloride ethyl acetate solution (0.5 ml), chloroform (1 ml) and methanol (1.5 ml)
  5. stirringthe reaction mixture was stirred at ambient temperature for 30 minutes
  6. customAfter evaporation of solvent
  7. 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-210f43c6dcf14118af8ce47ecb6dc170
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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