Hydrochloric Acid → HCID 58052343, compound

HRID 2190205Notes

Reaction equation

HRID 2190205 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18][Br:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH2:32][O:33][CH3:34].Cl>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:20])[C@@H:15]([CH2:32][O:33][CH3:34])[CH2:16][CH2:17][CH2:18][Br:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7864Chloromethyl Methyl EtherHCID 2724254Sodium bis(trimethylsilyl)amideHCID 108931642-Oxazolidinone, 3-(5-bromo-1-oxopentyl)-4-(phenylmethyl)-, (4S)-

Product 1

HCID 58052343HCID 58052343, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution (S)-4-benzyl-3-(5-bromopentanoyl)oxazolidin-2-one (4.00 g, 1 eq.) and THF (100 ml) was added NaHMDS (1 M in THF, 53 ml, 4.5 eq.) at −78° C. After 30 min chloro(methoxy)methane (12.3 g, 13 eq.) was added dropwise. The reaction mixture was stirred at −10° C. for 2 days. Concentrated aqueous HCl solution was carefully added. The resulting mixture was concentrated and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. Silica gel chromatography using 60-80% DCM-heptane yields the title compound (1.06 g, 23%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e4739c1878c4a3b82769c4b158a9945
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

Loading…