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

HRID 1080767ノート

反応式

HRID 1080767 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 atomosphere 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-dimethylformamide (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-d6469dc124a24cc38254cddc675a0bce
出典データセット
uspto-grants-1996_12
特許番号
US05583152

反応ノート

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