Dicyclohexylcarbodiimide → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

HRID 1088310Notes

Reaction equation

HRID 1088310 reaction equation
[CH3:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])=[CH:7][N:6]=1)([CH3:4])[CH3:3].[F:19][C:20]1[C:27]([F:28])=[C:26]([CH2:29][O:30][CH3:31])[C:25]([F:32])=[C:24]([F:33])[C:21]=1[CH2:22]O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:4][C:2]([C:5]1[N:6]=[CH:7][C:8]([CH:11]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([O:14][CH2:22][C:21]2[C:24]([F:33])=[C:25]([F:32])[C:26]([CH2:29][O:30][CH3:31])=[C:27]([F:28])[C:20]=2[F:19])=[O:13])=[CH:9][N:10]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 147187042-(2-Tert-butylpyrimidin-5-yl)-3,3-dimethylbutanoic acid

Product 1

HCID 147187502,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoic acid (0.1 q), 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol (0.089 g) and 4-dimethylaminopyridine (0.002 g) in dry dichloromethane (4 cm3) was stirred at the ambient temperature (20° C.) whilst N,N'-dicyclohexylcarbodiimide (0.084 g) was added in portions; the mixture was stirred for 18 hours. The solution was passed through silica gel and the silica gel eluted with, firstly, dichloromethane and, secondly a 50:1 mixture (by volume) of dichloromethane and ethyl acetate Evaporation of the solvents of the combined filtrate and eluted fractions gave the title compound (0.09 g) as a colourless oil.

Workup

  1. additionwas added in portions
  2. washthe silica gel eluted with, firstly, dichloromethane
  3. customsecondly a 50:1 mixture (by volume) of dichloromethane and ethyl acetate Evaporation of the solvents of the combined filtrate
  4. washeluted fractions

Sources & evidence

ORD record
ord-7587cdb749784e77acaf67434c242d04
Source dataset
uspto-grants-1990_10
Patent number
US04962109

Reaction notes

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