Dichloromethane → HCID 58169921, compound

HRID 384020Notes

Reaction equation

HRID 384020 reaction equation
O[C@@H:2]([C:6]1[CH:11]=CC=C[CH:7]=1)C(O)=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][NH:20]2)=[C:15]([CH3:26])[CH:14]=1.ClCCl.[C:30]([O-])([OH:32])=[O:31].[Na+]>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][N:20]2[C:30]([O:32][C:6]([CH3:2])([CH3:7])[CH3:11])=[O:31])=[C:15]([CH3:26])[CH:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 51002937HCID 51002937, compound

Product 1

HCID 58169921HCID 58169921, compoundYield 88%

Procedure

To a solution of (2S)-hydroxy(phenyl)ethanoic acid-(2R)-2-(4-fluoro-2-methylphenyl)-4-piperidinone (1:1) (WO 2008090117 published on 31 Jul. 2008) (50 g, 139 mmol) in dry Dichloromethane (DCM) (550 ml) TEA (29.1 ml, 209 mmol) was added and then BOC-Anhydride (38.8 ml, 167 mmol). The reaction mixture was stirred overnight at r.t. The reaction was diluted with NaHCO3 sat. sol. (400 ml) and two phases were separated. The organic layer was dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by a small pad of silica panel eluting with Cy to 7:3 Cy/EtOAc to afford the title compound (37.6 g, 122 mmol, 88% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.08-7.18 (m, 1H) 6.80-6.92 (m, 2H) 5.62 (br. s., 1H) 4.16-4.32 (m, 1H) 3.09-3.30 (m, 1H) 2.79 (d, 2H) 2.39-2.62 (m, 2H) 2.33 (s, 3H) 1.33-1.51 (m, 9H); UPLC: Rt=0.77 mins, m/z=251 [M−56+H]+.

Workup

  1. customwere separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by a small pad of silica panel
  6. washeluting with Cy to 7:3 Cy/EtOAc

Sources & evidence

ORD record
ord-ccd9e34c56894005990d3f9757c000ce
Source dataset
uspto-grants-2013_02
Patent number
US08367692B2

Reaction notes

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