Sodium Hydroxide → 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 275127ノート

反応式

HRID 275127 の反応式
Cl.[C:2]1([N+:8]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=CC=CC2C(=O)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1([O:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH3:41])[CH:36]=[C:35]3[CH2:42][C:43]2[CH:51]=[CH:50][C:46]([C:47]([OH:49])=[O:48])=[CH:45][C:44]=2[O:52][CH3:53])=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-:54].[Na+]>C(O)C>[C:17]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([O:48][C:47](=[O:49])[C:46]2[CH:50]=[CH:51][C:43]([CH2:42][C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([NH:31][C:29]([O:28][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)=[O:30])[CH:33]=4)[N:37]([CH3:41])[CH:36]=3)=[C:44]([O:52][CH3:53])[CH:45]=2)=[O:54])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 112931194-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acidHCID 86743328N,N-Diphenylcarbamoylpyridinium hydrochloride

生成物 1

HCID 867433274-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

N ,N-Diphenylcarbamoylpyridinium hydrochloride (0.132 g.) was added to a stirred solution of 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic acid (obtained as described in Example 9) (0.15 g.) and sodium hydroxide (0.35 ml. of 1M aqueous solution) in absolute ethanol (6 ml.), under an atmosphere of nitrogen. The mixture was stirred for 15 minutes, and was then partitioned between ethyl acetate (50 ml.) and water (30 ml.). The organic layer was washed successively with 1M hydrochloric acid (20 ml.) and saturated brine (20 ml.), then dried (MgSO4), and evaporated to give 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride, as a white foam. This foam was dissolved in N,N-di-methylformamide (DMF) (3 ml.), and added to a stirred solution of the sodium salt of benzenesulphonamide (0.19 g.) in DMF (6 ml.), under an atmosphere of nitrogen. The mixture was stirred for 1 hour and then poured into 1M hydrochloric acid (40 ml.). The acid mixture was extracted with ethyl acetate (2×30 ml.). The combined extracts were dried (MgSO4) and evaporated. The yellow oil obtained was purified by the following successive procedures:

後処理

  1. customwas then partitioned between ethyl acetate (50 ml.) and water (30 ml.)
  2. washThe organic layer was washed successively with 1M hydrochloric acid (20 ml.) and saturated brine (20 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated

出典と根拠

ORDレコード
ord-81a3c02f910d4d2bb1cd09cefeb917a4
出典データセット
uspto-grants-1995_02
特許番号
US05391758

反応ノート

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