Ethyl bromoacetate → 1-((S)-2-Benzyloxycarbonylaminopropyl)-1H-furo[2,3-g]indazole-7-carboxylic acid ethyl ester

HRID 1453891

반응식

HRID 1453891 반응식
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@@H:11]([CH3:25])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[C:20]=2[CH:22]=O)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH2:38]([O:37][C:35]([C:34]1[O:24][C:19]2=[CH:18][CH:17]=[C:16]3[C:21]([N:13]([CH2:12][C@@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:26])[CH3:25])[N:14]=[CH:15]3)=[C:20]2[CH:22]=1)=[O:36])[CH3:39]

참가 물질

7

반응물 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 136385114Benzyl [(1S)-2-(7-formyl-6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate

생성물 1

HCID 688576401-((S)-2-Benzyloxycarbonylaminopropyl)-1H-furo[2,3-g]indazole-7-carboxylic acid ethyl ester수율 42.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of the product from Step C (0.20 g, 0.56 mmol) in DMF (10 mL) was added potassium carbonate (0.23 g, 1.68 mmol) followed by ethyl 2-bromoacetate (0.07 mL, 0.62 mmol) at room temperature and the resultant solution was heated at 70° C. for 20 h. Saturated aqueous ammonium chloride (20 mL) was added followed by ethyl acetate (50 mL). The organic layer was separated and the aqueous was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated. The residue was purified by chromatography (silica, 50% ethyl acetate in hexane) to give an oil (0.10 g, 42%): MS(ES) m/z 422 (M+); 1H NMR (CDCl3) δ 8.17 (s, 1H), 8.05 (s, 1H), 7.72 (d, 1H, J=8.8 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.33 (m, 5H), 5.05-5.09 (m, 2H), 4.58 (m, 1H), 4.30 (m, 2H), 1.45 (t, 3H, J=7.2 Hz), 1.17 (d, 3H, J=6.8 Hz).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography (silica, 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-2feda30b31494016b4fe93da723e659e
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476687B2

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