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

HRID 440208
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HRID 440208 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine
촉매
HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-36b97a5701974288a083b8fb1a695e28
출처 데이터셋
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05518653

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