Water → HCID 59902314, compound

HRID 890680Notes

Reaction equation

HRID 890680 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].[NH4+].[Cl-].[OH2:20].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>C(Cl)(Cl)Cl>[CH:15]1([CH2:16][O:20][C:13]2[CH:14]=[C:15](/[CH:16]=[C:7](\[CH3:1])/[C:11]([N:8]3[C@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:11][O:10][C:9]3=[O:12])=[O:10])[CH:22]=[CH:21][C:25]=2[O:24][CH3:23])[CH2:13][CH2:14]1

Participants

7

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 59902314HCID 59902314, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-(R)-Phenyloxazolidin-2-one (33.0 g, 0.202 mol) was dissolved in THF (1 L) and cooled to −78° C. n-Butyl lithium (2.5 M in hexanes, 79.5 mL, 0.198 mol) was added, and the resulting reaction mixture was stirred for 20 minutes. A solution of Intermediate 62 (65.1 g, 0.213 mol) in THF (200 mL) was added dropwise over 15 minutes. The reaction mixture was stirred for 1 hour at −78° C., then warmed to 0° C., slowly. The reaction mixture became thick with beige solids. The mixture was neutralized at 0° C. with saturated NH4Cl (600 mL) and water (300 mL) The solution was warmed to 22° C. quickly and poured into CHCl3 (2400 mL). After shaking and separation, the organic layer was washed with water (1 L), saturated NaCl (1 L), dried over Na2SO4, and concentrated in vacuo to a pale orange solid (94.4 g).

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. stirringThe reaction mixture was stirred for 1 hour at −78° C.
  4. temperaturewas warmed to 22° C. quickly
  5. stirringAfter shaking
  6. customseparation
  7. washthe organic layer was washed with water (1 L), saturated NaCl (1 L)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo to a pale orange solid (94.4 g)

Sources & evidence

ORD record
ord-b73b2d144ce3450d86cd04570ff6c2b9
Source dataset
uspto-grants-2006_02
Patent number
US06998416B2

Reaction notes

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