Tetrahydrofuran → HCID 58109533, compound

HRID 2037561Notes

Reaction equation

HRID 2037561 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][C@@:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][CH:17]=2)[CH3:15])[CH2:9][CH2:8]1.[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[CH3:32][O:33][C:34]1[CH:30]=[CH:31][C:6]([CH2:7][O:3][CH2:4][CH2:5][CH2:6][C@@:7]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]3[CH:17]=[CH:18][C:19]([CH:22]=[CH2:23])=[CH:20][CH:21]=3)[CH3:15])[CH2:9][CH2:8]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 58109276HCID 58109276, compound

Product 1

HCID 58109533HCID 58109533, compound

Procedure

To a suspension of NaH (180 mg, 4.4 mmol) in THF (5 mL) was added a solution of (R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (800 mg, 2.2 mmol) in THF (10 mL) at 0° C. The resulting mixture was stirred for 30 min. Then PMBCI (520 mg, 3.3 mmol) was added to the above mixture. The mixture was stirred for 3 h. The reaction was quenched with aqueous NH4Cl solution. The organic phase was separated, and concentrated to give the crude (R)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one, which was used for the next step without purification (460 mg, 46%).

Workup

  1. additionThen PMBCI (520 mg, 3.3 mmol) was added to the above mixture
  2. stirringThe mixture was stirred for 3 h
  3. customThe reaction was quenched with aqueous NH4Cl solution
  4. customThe organic phase was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7b91b613c70416dab202982ee06508b
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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