Potassium Hydroxide → HCID 11398333, compound

HRID 731108Notes

Reaction equation

HRID 731108 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:15]3[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:21]([N:17]1[C:18]2[C:14](=[CH:13][C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:41])=[O:2])=[CH:7][CH:8]=3)=[CH:20][CH:19]=2)[C:15]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[C:16]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814804HCID 68814804, compound

Product 1

HCID 11398333HCID 11398333, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(1,3-dibenzyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.491 g, 0.913 mmol) was reacted with 1N KOH (1.8 ml) in THF/MeOH (6 ml/4 ml) to give the product (0.376 g, 0.713 mmol, 78%) as a white solid, mp 153-155° C. 1H NMR (DMSO-d6) δ 4.08 (s, 2H), 4.68 (s, 2H), 5.35 (s, 2H), 6.89 (d, J=7.2 Hz, 2H), 6.96 (d, J=8.9 Hz, 2H), 7.10-7.25 (m, 8H), 7.35 (dd, J=1.7, 8.5 Hz, 1H), 7.41-7.51 (m, 8H), 7.59 (d, J=1.1 Hz, 1H), 12.95 (broad s, 1H); IR (solid) 3020, 2900, 1750, 1600, 1520, 1470, 1450, 1430, 1350, and 1220 cm−1; [ESI(+)], m/z 524 (M+H)+; Anal. Calcd. for C36H29NO3.0.20H2O: C, 82.01; H, 5.62; N, 2.66; Found: C, 82.08, H, 5.58; N, 2.55.

Sources & evidence

ORD record
ord-1f8b82df2a8a4807a8a33ce6b4e52444
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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