Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-(2-methyl-1-oxoisoindolin-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216978ノート

反応式

HRID 216978 の反応式
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[NH2:16][C:17](=O)[C@@H:18]([NH:37][C:38]([C:40]1([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:39])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:35])[N:30]([CH3:36])[CH2:29]3)=[CH:22][CH:21]=1>ClCCl>[C:17]([C@@H:18]([NH:37][C:38]([C:40]1([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:51])([CH3:50])[CH3:52])[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:39])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:35])[N:30]([CH3:36])[CH2:29]3)=[CH:22][CH:21]=1)#[N:16]

参加物

4

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568583(S)-tert-Butyl 4-(1-amino-3-(4-(2-methyl-1-oxoisoindolin-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 59568607(S)-tert-Butyl 4-(1-cyano-2-(4-(2-methyl-1-oxoisoindolin-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate収率 62.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Burgess' reagent (638 mg) was added to (S)-tert-butyl 4-(1-amino-3-(4-(2-methyl-1-oxoisoindolin-5-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 31, step (iv), 718 mg) in dichloromethane (25 mL) at 20° C. under nitrogen. The resulting solution was stirred at room temperature for 17 h. The reaction mixture was diluted with dichloromethane, and washed with water. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude material. The crude product was purified by chromatography on silica eluting with methanol/ethyl acetate (0:100 to 5:95) to afford sub-titled compound (436 mg).

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude material
  6. customThe crude product was purified by chromatography on silica eluting with methanol/ethyl acetate (0:100 to 5:95)

出典と根拠

ORDレコード
ord-163d8597820746a4950cc52d7878a4e9
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

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