Dicyclohexylcarbodiimide → HCID 13102634, compound

HRID 544438Notes

Reaction equation

HRID 544438 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]1([CH3:29])[C@@H:19](/[CH:20]=[CH:21]/[C:22](=[O:25])[O:23][CH3:24])[C@H:18]1[C:26]([OH:28])=[O:27].[O:30]([C:37]1[S:38][C:39]([CH2:42]O)=[CH:40][N:41]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:16][C:17]1([CH3:29])[C@@H:19](/[CH:20]=[CH:21]/[C:22](=[O:25])[O:23][CH3:24])[C@H:18]1[C:26]([O:28][CH2:42][C:39]1[S:38][C:37]([O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:41][CH:40]=1)=[O:27]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13106154HCID 13106154, compoundHCID 18609509HCID 18609509, compound

Product 1

HCID 13102634HCID 13102634, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

0.1 g of 4-dimethylamino-pyridine and then 0.97 g of dicyclohexylcarbodiimide were added to a solution of 1 g of (1R,3S) 2,2-dimethyl-3-[(E) 3-oxo-3-methoxy-propen-1-yl)-cyclopropane-1-carboxylicacid in 20 ml of methylene chloride and the mixture was stirred at 20° C. for 15 minutes. A solution of 1.24 g of (2-phenoxy-5-thiazolyl)-methanol in 15 ml of methylene chloride was added dropwise at 10° C. to the mixture. The mixture was stirred at 20° C. for 4 hours and was filtered. The filtrate was treated with activated carbon, was washed with water, dried and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 hexane-ethyl acetate mixture yielded 1.09 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-[(E) 3-oxo-3-methoxy-propen-1-yl)-cyclopropane-1-carboxylate with a specific rotation of [α]D° =+60.5° (c=1.5% in benzene) and melting at 62° C.

Workup

  1. stirringThe mixture was stirred at 20° C. for 4 hours
  2. filtrationwas filtered
  3. additionThe filtrate was treated with activated carbon
  4. washwas washed with water
  5. customdried
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. customthe residue was chromatographed over silica gel
  9. washElution with an 8-2 hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-78889ab735cc4bd686594910b419d69a
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

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