HCID 10424733, compound → HCID 69031029, compound

HRID 277301Notes

Reaction equation

HRID 277301 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][C:17](Cl)=[O:18])[C:14](=[O:20])[O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26](=[O:35])[CH2:27][NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:24])([CH3:23])[CH3:22]>ClCCl.N1C=CC=CC=1.O.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][C:17]([N:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:35])=[O:18])[C:14](=[O:20])[O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 10424733HCID 10424733, compoundHCID 12433731HCID 12433731, compound

Product 1

HCID 69031029HCID 69031029, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%).

Workup

  1. customThe organic phase was separated
  2. washwashed successively with citric acid (10%, 2×100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow viscous oil

Sources & evidence

ORD record
ord-9ed19722dce2466ba405e2461645d274
Source dataset
uspto-grants-2002_03
Patent number
US06355683B1

Reaction notes

Loading…