Sodium Hydroxide → HCID 24765671, compound

HRID 2426987Notes

Reaction equation

HRID 2426987 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16]([NH:18][C@H:19]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH:9]=[CH:8]1.[OH-].[Na+]>C1COCC1.CO>[F:34][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:16]([NH:18][C@H:19]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH3:20])=[O:17])[CH:9]=[CH:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57908484HCID 57908484, compound

Product 1

HCID 24765671HCID 24765671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4-{(1S)-1-[({1-[3-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoate (220 mg, 0.458 mmol) was dissolved in THF (2 ml) and MeOH (1.14 ml). 2M NaOH (1.14 ml, 2.29 mmol) was added and the mixture stirred at 50° C. for 1 hour. The mixture was cooled, the organic solvents removed and poured into 1N HCl. The resulting solid was filtered and washed with water. 1H NMR (500 MHz, DMSO-d6): δ 12.90 (bs, 1H), 8.90 (d, 1H), 7.85 (d, 2H), 7.75 (d, 1H), 7.65-7.55 (m, 2H), 7.50-7.40 (m, 3H), 7.25 (m, 2H), 7.15-7.00 (m, 4H), 7.00 (d, 1H), 6.65 (s, 1H), 5.60 (dd, 2H), 5.00 (m, 1H), 1.20 (d, 3H). MS-ESI (464.9).

Workup

  1. temperatureThe mixture was cooled
  2. customthe organic solvents removed
  3. additionpoured into 1N HCl
  4. filtrationThe resulting solid was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-ab542aeaff1c4e37a97da43e0034dec2
Source dataset
uspto-grants-2011_06
Patent number
US07968578B2

Reaction notes

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