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

HRID 1439911Notes

Reaction equation

HRID 1439911 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: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

Participants

6

Reactant 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

Product 1

HCID 701259947-Chloro-3-[p-tert-butoxycarbonylaminomethyl-o-(carboxymethoxy)phenylcarbamoylmethyl]-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acidYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

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-27d85c73d17146bd8a6a9f91930d6022
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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