Diisopropylethylamine → HCID 480332、化合物

HRID 429968ノート

反応式

HRID 429968 の反応式
[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

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 49134011,3-Benzodioxole-5-sulfonyl chlorideHCID 21356686HCID 21356686、化合物

生成物 1

HCID 480332HCID 480332、化合物収率 73.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

[(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).

後処理

  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)

出典と根拠

ORDレコード
ord-5d81b1d948984e76a23b1a861bed61be
出典データセット
uspto-grants-2001_11
特許番号
US06319946B1

反応ノート

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