Methyl bromoacetate → HCID 54305290、化合物

HRID 502325ノート

反応式

HRID 502325 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OC(NC1C(=O)NC2C=CC=CC=2NC1)=O)(C)(C)C.BrCC(OC)=O>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:11](=[O:12])[CH:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9][NH:8][C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]1=2

参加物

7

反応物 4

HCID 60984Methyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 154908313-Tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-oneHCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

生成物 1

HCID 54305290HCID 54305290、化合物収率 83%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

(3(S)-tert-Butoxycarbonylamino-2-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)acetic acid methyl ester (103). A 1.0 M solution of lithium bis(trimethylsilyl)amide (3.4 ml, 3.4 mmol) in THF was added dropwise to a −78° C. solution of 3-tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one (0.94 g, 3.38 mmol) in 20 ml of anhydrous tetrahydrofuran and stirred for 30 minutes. Methyl bromoacetate (0.44 ml, 4 mmol) was added dropwise to the reaction mixture then warmed to room temperature. The reaction was diluted with 100 ml of ethyl acetate and washed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine. The combined organics were dried over anhydrous sodium sulfate, filtered, and evaporated to afford a gum that was purified by flash chromatography eluting with 3:7 EtOAc/Hex. to give 0.98 g (83%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.15-7.07 (2H, m), 6.98-6.94 (1H, m), 6.88-6.84 (1H, d), 5.62-5.55 (1H, d), 4.71-4.65 (1H, d), 4.65-4.6 (1H, m), 4.33-4.27 (1H, d), 3.96-3.90 (1H, m), 3.78 (3H, s), 3.44-3.37 (1H, m), 1.4 (9H, s).

後処理

  1. washwashed with 0.3N potassium hydrogen sulfate (50 ml), water (2×50 ml), and brine
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a gum that
  6. customwas purified by flash chromatography
  7. washeluting with 3:7 EtOAc/Hex

出典と根拠

ORDレコード
ord-57399eb203344c3f8dac98cef634a149
出典データセット
uspto-grants-2010_08
特許番号
US07772366B2

反応ノート

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