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 216978노트

반응식

HRID 216978 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-163d8597820746a4950cc52d7878a4e9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193239B2

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