Sodium hydride → 2-(4-(2-(p-Methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

HRID 1264551노트

반응식

HRID 1264551 반응식
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.[H-].[Na+].[C:13]([O:17][C:18](=[O:56])[CH:19]([N:24]1[C:30](=[O:31])[CH:29]([NH:32][C:33](=[O:51])[CH:34](Br)[CH2:35][CH2:36][CH2:37][CH2:38][N:39]2[C:43](=[O:44])[C:42]3=[CH:45][CH:46]=[CH:47][CH:48]=[C:41]3[C:40]2=[O:49])[CH2:28][C:27]2[CH:52]=[CH:53][CH:54]=[CH:55][C:26]=2[CH2:25]1)[CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13]([O:17][C:18](=[O:56])[CH:19]([N:24]1[C:30](=[O:31])[CH:29]([NH:32][C:33](=[O:51])[CH:34]([S:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:35][CH2:36][CH2:37][CH2:38][N:39]2[C:40](=[O:49])[C:41]3=[CH:48][CH:47]=[CH:46][CH:45]=[C:42]3[C:43]2=[O:44])[CH2:28][C:27]2[CH:52]=[CH:53][CH:54]=[CH:55][C:26]=2[CH2:25]1)[CH2:20][CH:21]([CH3:23])[CH3:22])([CH3:15])([CH3:16])[CH3:14]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 538847672-(4-(2-Bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

생성물 1

HCID 538676092-(4-(2-(p-Methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

Combine p-methoxybenzylmercaptan (0.08 mL, 0.57 mmol) and-sodium hydride (17 mg, 60% oil dispersion, 0.42 mmol) in degassed dimethylformamide (3 mL). After 1 hour, tetra-n-butylammonium iodide (about 5 mg) and 2-(4-(2-bromo-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester (0.27 mmol). After 20 hours, quench be the addition of a saturated aqueous ammonium chloride solution and dilute with water (about 5 mL). Extract with ethyl acetate (about 75 mL). Separate the layers and extract the orgainc layer with brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

후처리

  1. waitAfter 20 hours
  2. customquench
  3. additionthe addition of a saturated aqueous ammonium chloride solution
  4. additiondilute with water (about 5 mL)
  5. extractionExtract with ethyl acetate (about 75 mL)
  6. customSeparate the layers
  7. extractionextract the orgainc layer with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-9db7b64aea1c4681b0cb6c20704189e2
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544980B2

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