Pyridine → HCID 13041484, compound

HRID 1383190Notes

Reaction equation

HRID 1383190 reaction equation
N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:22][C:23]1([CH3:37])[C@@H:25](/[CH:26]=[C:27](\[F:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@H:24]1[C:34]([OH:36])=[O:35].[C:38]([C@@H:40](O)[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:42]=1)#[N:39]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:37][C:23]1([CH3:22])[C@@H:25](/[CH:26]=[C:27](\[F:33])/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C@H:24]1[C:34]([O:36][C@H:40]([C:38]#[N:39])[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([O:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:42]=1)=[O:35]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 11128112HCID 11128112, compound

Product 1

HCID 13041484HCID 13041484, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1.9 ml of pyridine and 4.8 g of dicyclohexylcarbodiimide were added to a solution of 4.9 g of (1R,cis) 2,2-dimethyl-3(Z)-[2-fluoro-2-ethoxycarbonyl-ethenyl]-cyclopropane-1-carboxylic acid in 39 ml of methylene chloride and a solution of 5.3 g of (S)α-cyano-3-phenoxy-benzyl alcohol in 9.8 ml of methylene chloride was added with stirring to the mixture. After stirring the mixture for 2 hours, 30 mg of 4-dimethylamino-pyridine were added thereto and the mixture was stirred for 2 hours. The mixture was cooled to 0° C. and was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was successively eluted with a 9-1 cyclohexane-ethyl acetate mixture and with a 6-4 methylene chloride-petroleum ether (b.p.=35°-70° C.) mixture to obtain 6.73 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3(Z)-[2-fluoro-2-ethoxycarbonyl-ethenyl]-cyclopropane-1-carboxylate with the same characteristics of the compound of Example 2.

Workup

  1. stirringAfter stirring the mixture for 2 hours
  2. stirringthe mixture was stirred for 2 hours
  3. filtrationwas filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas successively eluted with a 9-1 cyclohexane-ethyl acetate mixture and with a 6-4 methylene chloride-petroleum ether (b.p.=35°-70° C.) mixture

Sources & evidence

ORD record
ord-6d009803171c465bb69f7b8aaf184d9a
Source dataset
uspto-grants-1989_02
Patent number
US04808749

Reaction notes

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