Diisopropylethylamine → HCID 480332, 화합물

HRID 2074950노트

반응식

HRID 2074950 반응식
[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:30])[NH:9][C@@H:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:11]([OH:22])[CH2:12][NH:13][CH2:14][C:15]([CH3:21])([CH3:20])[CH2:16][CH2:17][C:18]#[N:19])[CH2:4][O:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[O:40]1[C:44]2[CH:45]=[CH:46][C:47]([S:49](Cl)(=[O:51])=[O:50])=[CH:48][C:43]=2[O:42][CH2:41]1>C(Cl)Cl>[O:1]1[CH2:6][CH:5]([O:7][C:8](=[O:30])[NH:9][C@@H:10]([CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@H:11]([OH:22])[CH2:12][N:13]([S:49]([C:47]2[CH:46]=[CH:45][C:44]3[O:40][CH2:41][O:42][C:43]=3[CH:48]=2)(=[O:50])=[O:51])[CH2:14][C:15]([CH3:21])([CH3:20])[CH2:16][CH2:17][C:18]#[N:19])[CH2:4][O:3][CH2:2]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 49134011,3-Benzodioxole-5-sulfonyl chlorideHCID 21356686HCID 21356686, 화합물

생성물 1

HCID 480332HCID 480332, 화합물수율 73.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

[(1S,2R)-1-Benzyl-3-(4-cyano-2,2-dimethyl-butylamino)-2-hydroxy-propyl]-carbamic acid [1,3]dioxan-5-yl ester (0.059 g, 0.14 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.075 ml, 0.42 mmol) and Benzo[1,3]dioxole-5-sulfonyl chloride (0.037 g, 0.17 mmol) at ambient temperature under argon with stirring. After 15 h the reaction mixture was concentrated in vacuo, taken up in EtOAc, washed with sat. aq. NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and solvent removed in vacuo. Purification by column chromatography (1% to 3% MeOH in CH2Cl2) gave 0.062 g of a white solid. MS (ES): 604 (M+1).

후처리

  1. concentrationAfter 15 h the reaction mixture was concentrated in vacuo
  2. washwashed with sat. aq. NaHCO3, and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customPurification by column chromatography (1% to 3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-f0c0ffa5fd9b41928398b8dda802c426
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919523B2

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