Dicyclohexylcarbodiimide → (2-phenoxy-4-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylate

HRID 615925Notes

Reaction equation

HRID 615925 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:30])[C@@H:19]([CH:20]=[C:21]2[CH2:25][CH2:24][S:23][C:22]2=[O:26])[C@H:18]1[C:27]([OH:29])=[O:28].[O:31]([C:38]1[S:39][CH:40]=[C:41]([CH2:43]O)[N:42]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:16][C:17]1([CH3:30])[C@@H:19]([CH:20]=[C:21]2[CH2:25][CH2:24][S:23][C:22]2=[O:26])[C@H:18]1[C:27]([O:29][CH2:43][C:41]1[N:42]=[C:38]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[S:39][CH:40]=1)=[O:28]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13106143HCID 13106143, compoundHCID 54175652(1R,3S) 3-[(dihydro-2-oxo-3(2H)-thienylidene)-methyl]-2,2-dimethyl-cyclopropane-1-carboxylic acid

Product 1

HCID 57141174(2-phenoxy-4-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylateYield 71.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.11 g of 4-dimethylamino-pyridine and 2 g of dicyclohexylcarbodiimide were added to a solution of 2.04 g of (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylic acid [described in French Pat. No. 70-21682] in 20 ml of methylene chloride and the mixture was stirred at 20° C. for 15 minutes. A solution of 1.7 g of (2-phenoxy-4-thiazolyl)-methanol in 10 ml of methylene chloride was added dropwise to the mixture which was stirred at 20° C. for 17 hours and was filtered. The organic phase of the filtrate was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel, and was eluted with an 8-2 cyclohexaneethyl acetate mixture to obtain 2.44 g of (2-phenoxy-4-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylate melting at 78° C.

Workup

  1. filtrationwas filtered
  2. washThe organic phase of the filtrate was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with an 8-2 cyclohexaneethyl acetate mixture

Sources & evidence

ORD record
ord-2c88bffd7782478b980cb54726ec71d6
Source dataset
uspto-grants-1985_02
Patent number
US04501894

Reaction notes

Loading…