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Methanol → 7-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid

HRID 1439911
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HRID 1439911 반응식
C1(S([N:10]2[C:18]3[CH:17]=[C:16]([Cl:19])[CH:15]=[C:14]4[CH2:20][CH2:21][CH:22]([CH2:23][C:24](=[O:50])[NH:25][C:26]5[CH:31]=[CH:30][C:29]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:28][C:27]=5[O:41][CH2:42][C:43]([O:45]C(C)(C)C)=[O:44])[C:12]([C:13]=34)=[C:11]2[C:51]([O:53]C)=[O:52])(=O)=O)C=CC=CC=1.CO.[Li+].[OH-].OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:19][C:16]1[CH:15]=[C:14]2[CH2:20][CH2:21][CH:22]([CH2:23][C:24](=[O:50])[NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])=[CH:28][C:27]=3[O:41][CH2:42][C:43]([OH:45])=[O:44])[C:12]3=[C:11]([C:51]([OH:53])=[O:52])[NH:10][C:18]([CH:17]=1)=[C:13]23
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참가 물질

6

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 18984723Methyl 1-benzenesulfonyl-7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

생성물 1

HCID 70125994
7-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid
수율 64.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 1-benzenesulfonyl-7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(tert-butoxycarbonylmethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (410 mg, 0.532 mmol) in a mixture of THF (6 mL ), MeOH (6 mL), and 1N LiOH (6 mL) was stirred for 17 h at room temperature, acidified to pH 2 with 5% KHSO4, and extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over magnesium sulfate, and concentrated. The residue was rinsed with diethyl ether and dried in vacuo to give 195 mg of the title compound (quant): 1H NMR (DMSO-d6) δ13.01 (br, 2H), 11.43 (s, 1H), 9.13 (s, 1H), 7.90 (d, 1H, J=8.3 Hz), 7.33 (d, 1H, J=6.3 Hz), 7.15 (s, 1H), 6.84 (s, 2H), 6.82 (d,1H, J=8.3 Hz), 4.05 (d, 2H, J=6.3 Hz), 3.88 (m, 1H), 3.32 (bs, 2H), 3.09 (mt, 1H, J=12.2 Hz), 2.79 (md, 1H, J=17.8 Hz), 2.68 (bd, 1H, J=13.9 Hz), 2.61 (bd, 1H, J=13.9 Hz), 2.09 (md 1H, J=14.2 Hz), 1.84 (m, 1H), 1.40 (s, 9H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was rinsed with diethyl ether
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-27d85c73d17146bd8a6a9f91930d6022
출처 데이터셋
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05496843

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