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

HRID 1080767노트

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HRID 1080767 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-d6469dc124a24cc38254cddc675a0bce
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05583152

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