Dicyclohexylcarbodiimide → HCID 14765987, compound

HRID 1769919Notes

Reaction equation

HRID 1769919 reaction equation
[CH2:1]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][N:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28](O)=[O:29].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[O:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28]([O:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:12]=[N:11][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:15][CH:14]=2)=[CH:21][CH:20]=1)=[O:29]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 14765985HCID 14765985, compound

Product 1

HCID 14765987HCID 14765987, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

901 mg (3 mmol) of 4-(2-n-octyloxy-5-pyrimidinyl)phenol, 464.5 mg (4 mmol) of (R)tetrahydrofuran-2-carboxylic acid and also 49 mg (0.4 mmol) of 4-dimethylaminopyridine are added at room temperature to a solution of 825 mg (4 mmol) of dicyclohexylcarbodiimide in 20 ml of dry dichloromethane while stirring. After stirring for 10 hours at room temperature, the reaction solution is evaporated down in vacuo. Chromatographic purification and recrystallization from n-hexane yield 710 mg (59%) of colorless crystals with [α]D25 =-8.8° (c=2, CHCl3).

Workup

  1. stirringAfter stirring for 10 hours at room temperature
  2. customthe reaction solution is evaporated down in vacuo
  3. customChromatographic purification and recrystallization from n-hexane yield 710 mg (59%) of colorless crystals with [α]D25 =-8.8° (c=2, CHCl3)

Sources & evidence

ORD record
ord-d954b9080f1f49f1a0ad2e147958f613
Source dataset
uspto-grants-1995_01
Patent number
US05384070

Reaction notes

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