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 1264551ノート

反応式

HRID 1264551 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9db7b64aea1c4681b0cb6c20704189e2
出典データセット
uspto-grants-2003_04
特許番号
US06544980B2

反応ノート

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