Lithium Hydroxide → HCID 68156863, compound

HRID 537550Notes

Reaction equation

HRID 537550 reaction equation
[CH:1]1([CH:5]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([N:29]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[N:30]3)=[C:24]([CH3:38])[CH:23]=2)[C:6]2[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH:13]=[CH:14][C:15]([O:17]C)=[O:16])=[O:11])=[CH:8][CH:7]=2)[CH2:4][CH2:3][CH2:2]1.[CH:39]1([CH:43]([O:58][C:59]2[CH:64]=[C:63]([CH3:65])[C:62]([N:66]3[CH:70]=[C:69]([C:71]([F:74])([F:73])[F:72])[CH:68]=[N:67]3)=[C:61]([CH3:75])[CH:60]=2)[C:44]2[CH:57]=[CH:56][C:47]([C:48]([NH:50][CH2:51][CH2:52][C:53]([OH:55])=[O:54])=[O:49])=[CH:46][CH:45]=2)[CH2:42][CH2:41][CH2:40]1.[OH-].[Li+]>C1COCC1>[CH:1]1([CH:5]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([N:29]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[N:30]3)=[C:24]([CH3:38])[CH:23]=2)[C:6]2[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[O:11])=[CH:8][CH:7]=2)[CH2:4][CH2:3][CH2:2]1.[CH:39]1([CH:43]([O:58][C:59]2[CH:64]=[C:63]([CH3:65])[C:62]([N:66]3[CH:70]=[C:69]([C:71]([F:74])([F:73])[F:72])[CH:68]=[N:67]3)=[C:61]([CH3:75])[CH:60]=2)[C:44]2[CH:57]=[CH:56][C:47]([C:48]([NH:50][CH2:51][CH2:52][C:53]([OH:55])=[O:54])=[O:49])=[CH:46][CH:45]=2)[CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 68156863HCID 68156863, compoundHCID 86701435HCID 86701435, compound

Product 2

HCID 68156863HCID 68156863, compoundHCID 86701434HCID 86701434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 3-(4-(cyclobutyl(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)methyl)benzamido)propenoate, Isomer 1 (450 mg, 0.85 mmol) in THF (4 mL) was added 2N aqueous lithium hydroxide (4 mL, 8.0 mmol). The resulting mixture was stirred at 20° C. for 1 h. THF was removed under reduced pressure. The residue was acidified by addition of 1N aqueous HCl to pH 3-4 and extracted with dichloromethane (20 mL*2). The organic layer was concentrated to give 3-(4-(cyclobutyl(3,5-dimethyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)methyl)benzamido)propenoic acid, Isomer 1 (330 mg) as a colorless solid. 1H NMR (400 MHz, Methanol-d4) δ 8.08 (s, 1H), 7.88 (s, 1H), 7.65 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 6.61 (s, 2H), 5.15 (d, J=7.2 Hz, 1H), 3.50 (t, J=6.8 Hz, 2H), 2.70-2.67 (m, 1H), 2.52 (t, J=6.8 Hz, 2H), 2.04-1.94 (m, 3H), 1.82-1.72 (m, 9H). MS (M+1)=516.1.

Workup

  1. customTHF was removed under reduced pressure
  2. additionThe residue was acidified by addition of 1N aqueous HCl to pH 3-4
  3. extractionextracted with dichloromethane (20 mL*2)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-2689fc1da849486cb3fa23e65d3c629b
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

Loading…