Potassium Carbonate → 2,5-Anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-1-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-D-arabino-hexitol

HRID 54815

반응식

HRID 54815 반응식
[NH2:1][CH2:2][C@H:3]1[O:8][C@H:7]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:5]([OH:6])[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:36]>O1CCCC1.O>[CH3:25][C:24]([Si:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:10][CH2:9][C@H:7]1[O:8][C@H:3]([CH2:2][NH:1][C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[O:36])[CH2:4][C@@H:5]1[OH:6])([CH3:27])[CH3:26]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 782054-Nitrobenzyl chloroformateHCID 677073761-Amino-2,5-anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol

생성물 1

HCID 677073312,5-Anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-1-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-D-arabino-hexitol수율 75.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A slurry of 3.15 g of product from Example 283 and 1.35 g of potassium carbonate in 15 ml of tetrahydrofuran at 0° C., under argon, is treated with 2.11 g of p-nitrobenzyl chloroformate and the reaction is stirred vigorously at 0° C. for 4 hours. The reaction mixture is diluted with 100 ml of water, extracted with 3×100 ml of ethyl acetate, dried, concentrated in vacuo and purified by chromatography (Silica Gel: 5-50% ethyl acetate/hexane) to give 3.49 g of the desired product.

후처리

  1. extractionextracted with 3×100 ml of ethyl acetate
  2. customdried
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography (Silica Gel: 5-50% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3d69db3f9af84b3f86f427f7889047bb
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623081

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