Nitrogen → (8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate

HRID 15746

반응식

HRID 15746 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH:12]2[CH2:23][OH:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.N#N.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][N:35]([CH3:39])[C:36](=[O:37])[O:24][CH2:23][CH:12]1[N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13]1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 59342380(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

생성물 1

HCID 59342408(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate수율 136.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol (111; 1.19 g, 3.18 mmol) and triethylamine (2.21 ml, 15.9 mmol) were added to CH2Cl2 (15 mL) in a flame-dried flask and placed tinder N2. DMAP (77.8 mg, 0.637 mmol) was added and the mixture stirred for 5 minutes. Dimethylcarbamoyl chloride (0.88 mL, 1.54 mmol) was added dropwise and the reaction stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water were added. The aqueous layer was extracted with several more portions of EtOAc. The combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine, dried over Na2SO4 and concentrated to yield 940 mg of 112 as a yellow oil. The material was purified by column chromatography using EtOAc/hexanes gradients to yield 836 mg (59%) of a mixture of cis/trans isomers.

후처리

  1. stirringthe reaction stirred for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water
  3. additionwere added
  4. extractionThe aqueous layer was extracted with several more portions of EtOAc
  5. washThe combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2d6a559f17e04d37922fd5bb09eb2b92
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732609B2

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