methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylate → [3-cyclohexyl-6-(methoxycarbonyl)-2-(4-methoxyphenyl)-1H-indol-1-yl]acetic acid

HRID 1713930Notes

Reaction equation

HRID 1713930 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[C:10]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:9]1[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[CH:21]1([C:10]2[C:11]3[C:16](=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 11340537methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 11189363[3-cyclohexyl-6-(methoxycarbonyl)-2-(4-methoxyphenyl)-1H-indol-1-yl]acetic acidYield 95%

Conditions

Temperature
25 °C

Procedure

A solution (0.4 M) of methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(4-methoxyphenyl)-1H-indole-6-carboxylate (from Step 2) in a 1:1 mixture of CH2Cl2/TFA was stirred at 25° C. for 4 h. The mixture was concentrated and the residue was triturated with Et2O to afford the title compound (95%) as a solid. 1H NMR (300 MHz, DMSO-d6, 300K) δ 1.13-1.36 (m, 3H), 1.62-1.95 (m, 7H), 2.56-2.67 (m, 1H), 3.86 (s, 3H), 3.89 (s, 3H), 4.74 (s, 2H), 7.12 (d, J 8.6, 2H), 7.28 (d, J 8.6, 2H), 7.69 (dd, J 8.5, 1.2, 1H), 7.86 (d, J 8.5, 1H), 8.02 (d, J 1.2, 1H), 12.98 (bs, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-82a6514f9158433183303e11c7ad4ee2
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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