Ethyl Acetate → 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904468노트

반응식

HRID 1904468 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([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH3:42])[CH:36]=[C:35]3[CH2:43][C:44]2[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[CH:46][C:45]=2[O:53][CH3:54])=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+].C(OCC)(=[O:59])C>CO.CN(C)C=O>[C:17]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([O:49][C:48](=[O:50])[C:47]2[CH:51]=[CH:52][C:44]([CH2:43][C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([NH:31][C:29](=[O:30])[CH2:28][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[CH:33]=4)[N:37]([CH2:41][CH3:42])[CH:36]=3)=[C:45]([O:53][CH3:54])[CH:46]=2)=[O:59])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 146268494-[5-(2-Cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic acidHCID 86743117N,N-diphenylcarbamoylpyridinium chloride

생성물 1

HCID 867431194-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6228Dimethylformamide용매

실험 절차

A solution of N,N-diphenylcarbamoylpyridinium chloride (311 mg) in methanol (1 ml) was added to a stirred solution of the acid (J) (450 mg) and sodium hydroxide (1 ml of a 1M aqueous solution) in methanol (4 ml) under an atmosphere of nitrogen. After stirring for 1.5 minutes, ethyl acetate and N,N-dimethylformamide (2 ml) were added and the mixture allowed to stir until all dissolved. The ethyl acetate solution was washed with water and saturated brine, dried (MgSO4) and evaporated to give a quantitative yield of 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (E) as a crusty foam; partial NMR: (80 MHz, DMSO-d6): 1.30(t, J=7.1 Hz, 2H, NCH2CH3), 3.84(s, 3H, OCH3), 3.94(s, 2H, ArCH2), 4.05(q, J=7.1 Hz, 2H, NCH2CH3), 7.41(s, 10H, NArH), 9.56(s, 1H, CONH).

후처리

  1. stirringto stir until all dissolved
  2. washThe ethyl acetate solution was washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-1d1426579a924c6e9b608c04d3fd6f32
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837235

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