Methyl bromoacetate → HCID 54305290, 화합물

HRID 502325노트

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HRID 502325 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 54305290HCID 54305290, 화합물수율 83%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-57399eb203344c3f8dac98cef634a149
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772366B2

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