Lithium Hydroxide → HCID 44624208, compound

HRID 2274078Notes

Reaction equation

HRID 2274078 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[NH:17][C:16]5[CH:21]([CH2:24][C:25]([O:27]CC)=[O:26])[CH2:22][CH2:23][C:15]=5[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:32]([F:35])([F:34])[F:33])[CH2:3][CH2:2]1.[Li+].[OH-]>O1CCOCC1.CCOC(C)=O>[CH:1]1([CH2:4][O:5][C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[NH:17][C:16]5[CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:22][CH2:23][C:15]=5[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:32]([F:35])([F:33])[F:34])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67211429HCID 67211429, compound

Product 1

HCID 44624208HCID 44624208, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-(7-(4-(cyclopropylmethoxy)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (22.9 mg, 0.047 mmol) in dioxane was added 1M LiOH (0.188 mL, 0.188 mmol). The reaction mixture was stirred 3 h, taken up in EtOAc and washed with 1 M HCl. The EtOAc extract was dried over MgSO4 and concentrated. The residue was purified by preparative HPLC/MS to give the title compound as a solid. LCMS m/z=460.3 [M±H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.30-0.38 (m, 2H), 0.52-0.59 (m, 2H), 1.17-1.27 (m, 1H), 2.03-2.13 (m, 1H), 2.35 (dd, J=15.98, 8.91 Hz, 1H), 2.59-2.76 (m, 4H), 3.99 (d, J=6.69 Hz, 2H), 5.05 (s, 2H), 6.69 (dd, J=8.84, 2.40 Hz, 1H), 6.91 (d, J=2.53 Hz, 1H), 7.19 (d, J=8.72 Hz, 1H), 7.24 (d, J=8.46 Hz, 1H), 7.62-7.71 (m, 2H), 10.45 (s, 1H).

Workup

  1. washwashed with 1 M HCl
  2. extractionThe EtOAc extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC/MS

Sources & evidence

ORD record
ord-3f693777ef2e4cdfbd92e8d89f3ea4c6
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

Loading…