Water → HCID 50905520, compound

HRID 1422647Notes

Reaction equation

HRID 1422647 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([N:13]2[CH2:18][CH2:17][C:16]([CH2:25][C:26]3([CH3:29])[CH2:28][O:27]3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:15][C:14]2=[O:30])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.O>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([N:13]2[CH2:18][CH2:17][C:16]([CH2:25][C:26]([OH:27])([CH3:29])[CH3:28])([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:15][C:14]2=[O:30])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 86669140HCID 86669140, compound

Product 1

HCID 50905520HCID 50905520, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of crude 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-((2-methyloxiran-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (18 mg, ≦0.038 mmol) in dry THF (2 mL) was cooled in an ice bath and 1 M LiEt3BH in THF (0.2 mL, 0.2 mmol) was added. The mixture was stirred in the ice bath for 3 h and 30% H2O (1 mL) and water (5 mL) were added. The mixture was diluted with EtOAc (90 mL), washed with brine (10 mL), 30% aq Na2S2O3 (10 mL) and brine (10 mL), and dried over Na2SO4. Removal of the solvent left an oil (17 mg) which was purified by prep HPLC to afford 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (6.9 mg) as an oil. LC-MS Method 1 tR=1.90 min, m/z=; 1H NMR (CDCl3) δ 1.06 (s, 3H), 1.19 (s, 3H), 1.74 (s, 3H), 1.80 (s, 3H), 2.23 (s, 2H), 2.32 (m, 2H), 2.65 (br s, 1H), 2.91 (m, 1H), 3.62 (m, 1H), 6.97 (m, 2H), 7.25-7.45 (7H).

Workup

  1. washwashed with brine (10 mL), 30% aq Na2S2O3 (10 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent
  4. waitleft an oil (17 mg) which
  5. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-09de9c5b72144203b22e5731e8a8ab28
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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