Water → HCID 58109235, compound

HRID 2037426Notes

Reaction equation

HRID 2037426 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]([N:10]2[CH2:15][CH2:14][C:13]([CH3:22])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:23])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].O>CC#N.C(Cl)Cl>[CH3:22][C:13]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:12][C:11](=[O:23])[N:10]([C@H:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[O:1][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:9])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 58109491HCID 58109491, compound

Product 1

HCID 58109235HCID 58109235, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R/S)-3-((S)-1-(3-hydroxyphenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (0.0955 g, 0.31 mmol, 1.0 equiv), Cs2CO3 (0.3307 g, 1.01 mmol, 3.3 equiv), and ethyl bromoacetate (0.1468 g, 0.88 mmol, 2.8 equiv) in CH3CN (1.5 mL) was stirred at rt for 3 d. The mixture was diluted with CH2Cl2, treated with H2O (2 mL), dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 0.1025 g (84%) of ethyl 2-(3-((S)-1-((R/S)-6-methyl-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenoxy)acetate. LC-MS Method 1, tR=1.75 min, m/z=398 (M+1). 1H NMR (CDCl3) 7.40-7.23 (m, 6H), 6.95-6.93 (m, 1H), 6.88 (m, 1H), 6.81-6.78 (m, 1H), 5.76 (q, J=7.1 Hz, 1H), 4.61 (s, 2H), 4.27 (q, J=7.1 Hz, 2H), 2.68-2.65 (m, 2H), 2.28-2.23 (m, 1H), 2.06-1.98 (m, 1H), 1.63 (s, 3H), 1.30 (t, J=7.2 Hz, 3H), 1.26 (d, J=7.3 Hz, 3H).

Workup

  1. dry with materialdried over Na2SO4
  2. customAfter the solvents were evaporated
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-dc110884afcc4f7da5f3946b04942247
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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