Dicyclohexylcarbodiimide → 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid 4-picolylamide

HRID 232137Notes

Reaction equation

HRID 232137 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:14]([CH:20]=[C:21]([CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[C:22](O)=[O:23])[O:13][C:12]1([CH3:35])[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH2:43])=[CH:38][CH:37]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH:43][C:22](=[O:23])[C:21]([CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)=[CH:20][C@@H:14]2[O:13][C:12]([CH3:35])([CH3:34])[N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[C@H:15]2[CH2:16][CH:17]([CH3:18])[CH3:19])=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 773174-PyridinemethanamineHCID 700453933-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid

Product 1

HCID 700459133-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid 4-picolylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

98 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid was dissolved in 0.4 ml of dry dichloromethane, and 21 μl of 4-picolylamine, 30 mg of 1-hydroxybenzotriazole and 45 mg of N,N'-dicyclohexylcarbodiimide were added thereto at 0° C. under stirring. The mixture was stirred at 0° C. for 2 hours and then at room temperature overnight. Insolubles were filtered off, and 20 ml of ethyl acetate was added. The mixture was washed with a saturated sodium hydrogencarbonate aqueous solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (2 g of Kieselgel 60) by using chloroform/methanol (20/1) to obtain 121 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid 4-picolylamide as a colorless oily substance.

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hours
  2. customat room temperature
  3. customovernight
  4. filtrationInsolubles were filtered off
  5. addition20 ml of ethyl acetate was added
  6. washThe mixture was washed with a saturated sodium hydrogencarbonate aqueous solution
  7. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (2 g of Kieselgel 60)

Sources & evidence

ORD record
ord-d31da6d6f935439b9f111c2bc2989e19
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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