Hydrochloric Acid → ((S)-7-tert-Butoxycarbonylamino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester

HRID 30992ノート

反応式

HRID 30992 の反応式
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]2[CH:20]=[CH:21][CH:22]=[CH:23][C:9]1=2)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].Cl>CN(C=O)C>[CH3:32][O:31][C:29](=[O:30])[CH2:28][N:13]1[C:14](=[O:15])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:24])[C:9]2[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=2[C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]1=2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 58972520((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 58972533((S)-7-tert-Butoxycarbonylamino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester (284 mg, 0.88 mmol) were diluted in DMF (5 ml) and treated with sodium hydride (60 mg of 60% suspension in mineral oil, 1.5 mmol). After stirring for 30 minutes, methyl bromoacetate (0.14 ml, 1.5 mmol) were added and the solution stirred for another 6 h. The pH is adjusted to 1.5 with 2N hydrogen chloride and extracted with ethyl acetate (10 ml). After back-extraction of the aqueous phases with ethyl acetate, the combined organic phases were washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated to dryness. After chromatography (silica, eluent cyclohexane/ethyl acetate 88/12), the product was obtained as off-white viscous oil (63%); MS: m/e=397(M+H+).

後処理

  1. stirringthe solution stirred for another 6 h
  2. extractionextracted with ethyl acetate (10 ml)
  3. extractionAfter back-extraction of the aqueous phases with ethyl acetate
  4. washthe combined organic phases were washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-4c58fcf5c52a401e86542ea305c6ac9d
出典データセット
uspto-grants-2008_09
特許番号
US07425551B2

反応ノート

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