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

HRID 1453891

反応式

HRID 1453891 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2feda30b31494016b4fe93da723e659e
出典データセット
uspto-grants-2009_01
特許番号
US07476687B2

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