Dicyclohexylcarbodiimide → HCID 57009741, compound

HRID 544427Notes

Reaction equation

HRID 544427 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].[CH2:31]([C:38]1[S:39][C:40]([CH2:43]O)=[CH:41][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:40]1[S:39][C:38]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:42][CH:41]=1)=[O:28]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 20406889(2-Benzyl-5-thiazolyl)-methanolHCID 54175652HCID 54175652, compound

Product 1

HCID 57009741HCID 57009741, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.1 g of 4-dimethylamino-pyridine and 0.94 g of dicyclohexylcarbodiimide were added to a solution of 1.1 g of (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylic acid in 10 ml of methylene chloride and then a solution of 1 g of (2-benzyl-5-thiazolyl)-methanol in 12 ml of methylene chloride was added to the mixture. The mixture was stirred for 17 hours at 20° C. and was filtered and the organic filtrate was washed with water, dried and evaporated to dryness under reduced pressure. The residue was taken upin 8 ml of a 7-3 cyclohexane-ethyl acetate mixture and the mixture was filtered. The filtrate was chromatographed over silica gel and was eluted with a 7-3 cyclohexane-ethyl acetate mixture to obtain 0.97 g of (2-benzyl -5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(dihydro-2-oxo-3-(2H)-thienylidene)-methyl]-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =+38°±2° (c=0.5% in benzene).

Workup

  1. filtrationwas filtered
  2. washthe organic filtrate was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. filtrationthe mixture was filtered
  6. customThe filtrate was chromatographed over silica gel
  7. washwas eluted with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-dc8298e3517842cf9f465e0eaab85819
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

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