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N-Acetylsulfanilyl chloride → [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[(4-acetamidophenyl)sulfonyl-(4-cyano-2,2-dimethyl-butyl)amino]-1-benzyl-2-hydroxy-propyl]carbamate

HRID 1167259
ノート
印刷プレビュー

反応式

HRID 1167259 の反応式
[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:32])[NH:11][C@@H:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([OH:24])[CH2:14][NH:15][CH2:16][C:17]([CH3:23])([CH3:22])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1.C(N(C(C)C)CC)(C)C.[C:42]([NH:45][C:46]1[CH:51]=[CH:50][C:49]([S:52](Cl)(=[O:54])=[O:53])=[CH:48][CH:47]=1)(=[O:44])[CH3:43]>C(Cl)Cl>[O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:32])[NH:11][C@@H:12]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@H:13]([OH:24])[CH2:14][N:15]([S:52]([C:49]2[CH:48]=[CH:47][C:46]([NH:45][C:42](=[O:44])[CH3:43])=[CH:51][CH:50]=2)(=[O:54])=[O:53])[CH2:16][C:17]([CH3:22])([CH3:23])[CH2:18][CH2:19][C:20]#[N:21])[CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 81531DiisopropylethylamineHCID 59815752[(1S, 2R)-1-Benzyl-3-(4-cyano-2,2-dimethylbutylamino)-2-hydroxy-propyl]-carbamic acid (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester

生成物 1

HCID 480326[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(1S,2R)-3-[(4-acetamidophenyl)sulfonyl-(4-cyano-2,2-dimethyl-butyl)amino]-1-benzyl-2-hydroxy-propyl]carbamate収率 18.7%

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 (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-yl ester (0.020 g, 0.05 mmol) was dissolved in CH2Cl2 and treated with diisopropylethylamine (0.016 ml, 0.09 mmol) and 4-acetamidobenzenesulfonyl chloride (0.011 g, 0.05 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 preparative thin layer chromatography (EtOAc) gave 0.006 g of a white solid. MS (ES): 643 (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 preparative thin layer chromatography (EtOAc)

出典と根拠

ORDレコード
ord-b40d0f8f8a3648cfba2de333d308e27b
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06617350B2

反応ノート

読み込み中…

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