Ethanol → HCID 59643350, compound

HRID 2251573Notes

Reaction equation

HRID 2251573 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:48]=[CH:47][C:12]([CH2:13][N:14]([C:32]4[N:36]=[C:35]([C:37]5[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=5)[O:34][N:33]=4)[CH2:15][CH2:16][C:17]4[CH:31]=[CH:30][C:20]([O:21][C:22]([CH3:29])([CH3:28])[C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=4)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.CCO.O.[Li+].[OH-]>C1COCC1>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:48]=[CH:47][C:12]([CH2:13][N:14]([C:32]4[N:36]=[C:35]([C:37]5[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:44])([F:45])[F:46])[CH:38]=5)[O:34][N:33]=4)[CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][C:20]([O:21][C:22]([CH3:29])([CH3:28])[C:23]([OH:25])=[O:24])=[CH:30][CH:31]=4)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 69099654HCID 69099654, compound

Product 1

HCID 59643350HCID 59643350, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-{4-[2-([4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]{5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}amino)ethyl]phenoxy}-2-methylpropanoate (93 mg, 0.14 mmol) in anhydrous THF (1.5 ml) was added EtOH (0.4 ml), water (0.4 ml), and LiOH (31 mg, 1.28 mmol). The mixture was stirred at rt for 12 h. The reaction was quenched with a solution of saturated aqueous KH2PO4, and the aqueous phase was extracted with EtOAc (3×20 ml). The combined organic phases were dried with Na2SO4 and concentrated in vacuo to yield the title compound as a colorless solid (58 mg, 65%). 1H NMR (CDCl3) δ 8.34 (s, 1H), 8.26 (d, 1H, J=7.9), 7.80 (d, 1H, J=7.8), 7.65 (s, 1H), 7.62 (d, 1H, J=8.0), 7.40 (d, 2H, J=8.1), 6.92 (d, 2H, J=8.3), 6.81 (d, 2H, J=8.5), 6.65 (d, 2H, J=8.4), 4.53 (s, 2H), 3.63 (t, 2H, J=6.2), 2.92 (t, 2H, J=6.4), 2.21 (m, 1H), 1.58 (s, 6H), 1.19–1.06 (m, 4H). MS: m/z 633 (M+1).

Workup

  1. customThe reaction was quenched with a solution of saturated aqueous KH2PO4
  2. extractionthe aqueous phase was extracted with EtOAc (3×20 ml)
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ed2386a349849e1a3ba93b9d2f8c801
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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