1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate

HRID 1085709Notes

Reaction equation

HRID 1085709 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][C:14]1[N:19]=[CH:18][C:17]([CH:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([OH:23])=[O:22])=[CH:16][N:15]=1.[CH3:28][O:29][CH2:30][C:31]1[C:38]([F:39])=[C:37]([F:40])[C:34]([CH2:35]O)=[C:33]([F:41])[C:32]=1[F:42]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:13][C:14]1[N:19]=[CH:18][C:17]([CH:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:21]([O:23][CH2:35][C:34]2[C:33]([F:41])=[C:32]([F:42])[C:31]([CH2:30][O:29][CH3:28])=[C:38]([F:39])[C:37]=2[F:40])=[O:22])=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111721164-Methoxymethyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 14718723(RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid

Product 1

HCID 147187732,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoateYield 38.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.276 g) in dry dichloromethane (6 cm3) was added to a stirred solution of (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid (0.3 g) and 4-(methoxymethyl)-2,3,5,6-tetrafluorobenzylalcohol (0.33 g) containing a catalytic amount of 4-(N,N'-dimethylamino) pyridine. The stirred mixture was maintained at the ambient temperature for 2 hours, and left to stand overnight. The reaction solution was washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using a 1:1 (by volume) mixture of ethyl acetate and dichloromethane as eluent to give 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate (0.228 g) as a yellow oil.

Workup

  1. waitleft
  2. washThe reaction solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated by evaporation of the solvent under reduced pressure
  5. additiona 1:1 (by volume) mixture of ethyl acetate and dichloromethane as eluent

Sources & evidence

ORD record
ord-fce2e2cfac8f48d1a01b85503b024ca7
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

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