Methanol → HCID 18984740, compound

HRID 1439907Notes

Reaction equation

HRID 1439907 reaction equation
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:46])[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[CH2:41][C:42]([O:44]C)=[O:43])[C:12]([C:13]=34)=[C:11]2[C:47]([O:49]C)=[O:48])(=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:46])[NH:25][C:26]3[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]=3[CH2:41][C:42]([OH:44])=[O:43])[C:12]3=[C:11]([C:47]([OH:49])=[O:48])[NH:10][C:18]([CH:17]=1)=[C:13]23

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 18984738HCID 18984738, compound

Product 1

HCID 18984740HCID 18984740, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-benzenesulfonyl-7-chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(methoxycarbonylmethyl)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (300 mg, 0.414 mmol) in a mixture of THF (5 mL), MeOH (5 mL), and 1N LiOH (5 mL) was stirred for 19 h at room temperature, acidified to pH 3 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 150 mg of the title compound (quant): 1H NMR (DMSO-d6) δ12.54 (br, 2H), 11.42 (s, 1H), 9.33 (s, 1H), 7.37 (d, 1H, J=7.9 Hz), 7.35 (s, 1H), 7.13 (d, 1H, J=7.9 Hz), 7.10 (s, 2H), 6.83 (s, 1H), 4.08 (d, 2H, J=7.9 Hz), 3.88 (m, 1H), 3.59 (d, 1H, J=16.3 Hz), 3.55 (d, 1H, J=16.3 Hz), 3.09 (mr, 1H, J=14.0 Hz), 2.81 (md, 1H, J=16.8 Hz), 2.64 (dd, 1H, J=14.0, 3.5 Hz), 2.53 (m, 1 H), 2.09 (md, 1, H, J=12.2 Hz), 1.83 (m, 1H), 1.40 (s, 9H).

Workup

  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

Sources & evidence

ORD record
ord-27b64c3cf4204e8d958b560c6ebc7ba9
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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