Dicyclohexylcarbodiimide → 1-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-[(S)-2-fluorohexanoyloxy]benzene

HRID 440208Notes

Reaction equation

HRID 440208 reaction equation
[CH2:1]([C@H:9]1[CH2:14][O:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[O:11][C@@H:10]1[CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:23][C@@H:24]([CH2:28][CH2:29][CH2:30][CH3:31])[C:25](O)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C@H:9]1[CH2:14][O:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:25](=[O:26])[C@@H:24]([F:23])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:17][CH:16]=2)[O:11][C@@H:10]1[CH3:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13683897(S)-2-fluorocaproic acidHCID 677427334-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol

Product 1

HCID 536797291-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-[(S)-2-fluorohexanoyloxy]benzeneYield 76.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 380 mg of 4-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]phenol, 185 mg of (S)-2-fluorocaproic acid, 333 mg of N,N'-dicyclohexylcarbodiimide, 20 mg of 4-(dimethylamino)pyridine and 40 ml methylene chloride was stirred at room temperature under nitrogen for 16.5 hours. Subsequently, the suspension was filtered and the filtrate was evaporated on a rotary evaporator. The crude product (1.0 g) was suspended in 50 ml of methylene chloride, the suspension was filtered and the filtrate was evaporated. Recrystallization of the white, solid residue (0.5 g) from hexane gave 0.4 g of 0.4 g of 1-[(2S,4R,5S)-5-octyl-4-methyl-1,3-dioxan-2-yl]-4-[(S)-2-fluorohexanoyloxy]benzene as white crystals with m.p. (C-I) 58.8° C. and [a]D =+16.7° (c=1% in chloroform).

Workup

  1. filtrationSubsequently, the suspension was filtered
  2. customthe filtrate was evaporated on a rotary evaporator
  3. filtrationthe suspension was filtered
  4. customthe filtrate was evaporated
  5. customRecrystallization of the white, solid residue (0.5 g) from hexane

Sources & evidence

ORD record
ord-36b97a5701974288a083b8fb1a695e28
Source dataset
uspto-grants-1996_05
Patent number
US05518653

Reaction notes

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