Lithium Hydroxide → HCID 44624272, compound

HRID 2274066Notes

Reaction equation

HRID 2274066 reaction equation
[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][C:15]4[CH:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:21][CH2:22][C:14]=4[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Li+].[OH-]>O1CCOCC1>[CH3:1][S:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[NH:16][C:15]4[CH:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][CH2:22][C:14]=4[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67220437HCID 67220437, compound

Product 1

HCID 44624272HCID 44624272, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the stirred solution of ethyl 2-(7-(4-(methylsulfonyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (40 mg, 0.094 mmol) in dioxane was added 1M LiOH aqueous solution (0.47 mL, 0.47 mmol). The reaction mixture was stirred at room temperature for 24 h. The solvent was partly removed, diluted with water, and acidified with HCl solution. The pinkish solid was collected and dried to give the title compound (26 mg). LCMS m/z=400.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.04-2.08 (m, 1H), 2.35 (dd, J=16.0 and 9.0 Hz, 1H), 2.63-2.75 (m, 4H), 3.20 (s, 3H), 3.45-3.50 (m, 1H), 5.21 (s, 2H), 6.73 (dd, J=8.7 and 2.4 Hz, 1H), 6.92 (d, J=2.4 Hz, 1H), 7.20 (d, J=8.7 Hz, 1H), 7.71 (d, J=8.3 Hz, 2H), 7.92 (d, J=8.3 Hz, 2H), 10.47 (s, 1H), 12.18 (s, 1H).

Workup

  1. customThe solvent was partly removed
  2. additiondiluted with water
  3. customThe pinkish solid was collected
  4. customdried

Sources & evidence

ORD record
ord-db5ae139f1c44b7ea7b297957f9f2405
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

Loading…