Sodium Bicarbonate → HCID 58870787, compound

HRID 1927629Notes

Reaction equation

HRID 1927629 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[C:6]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:33])[CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:22][C:21]=2[F:34])[CH2:16][CH2:15]1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:31]([CH:28]([CH2:29][CH3:30])[C:27]([NH:26][C:23]1[CH:24]=[CH:25][C:20]([N:17]2[CH2:16][CH2:15][CH:14]([C:6]([OH:13])([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:2][CH2:3][CH2:4][CH3:5])[CH2:19][CH2:18]2)=[C:21]([F:34])[CH:22]=1)=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 69304073HCID 69304073, compoundHCID 178418339Butyllithium

Product 1

HCID 58870787HCID 58870787, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of n-BuLi (1 mL, 2.5 M in hexanes) in THF (10 mL) at −78° C., N-[4-(4-benzoyl-piperidin-1-yl)-3-fluoro-phenyl]-2-ethyl-butyramide (200 mg, 0.50 mmol) in THF (10 mL) was added. After 10 min, the mixture was warmed to 25° C. and diluted with satd. aq. NaHCO3 (10 mL). The mixture was extracted with EtOAc, and the organic layer was concentrated and purified by PTLC to provide the title compound (130 mg, 57%). MS: 455.4. 1H NMR (CDCl3): 7.42-7.15 (m, 7H), 6.84 (t, J=9.1, 1H), 3.42 (d, J=11.7, 1H), 3.32 (d, J=11.7, 1H), 2.61-2.45 (m, 2H), 2.01-1.82 (m, 4H), 1.78-1.62 (m, 3H), 1.61-1.41 (m, 6H), 1.32-1.15 (m, 4H), 0.98-0.80 (m, 9H).

Workup

  1. additiondiluted with satd
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic layer was concentrated
  4. custompurified by PTLC

Sources & evidence

ORD record
ord-a7b6a342c26448b8897b0298a7941b61
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

Loading…