HCID 58109670, compound → HCID 58109698, compound

HRID 2037565Notes

Reaction equation

HRID 2037565 reaction equation
COC1C=CC(C[O:8][CH2:9][CH2:10][CH2:11][C@@:12]2(C3C=CC=CC=3)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27]C(OC)=O)=[CH:23][CH:22]=3)[CH3:20])[CH2:14][CH2:13]2)=CC=1.C[Mg]Br>C1COCC1>[OH:17][C:12]([CH3:13])([CH3:11])[CH2:27][C:24]1[CH:23]=[CH:22][C:21]([C@@H:19]([N:15]2[CH2:14][CH2:13][C@:12]([CH2:11][CH2:10][CH2:9][OH:8])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:16]2=[O:18])[CH3:20])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 58109670HCID 58109670, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58109698HCID 58109698, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-((S)-1-((R)-6-(3-(4-methoxybenzyloxy)propyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)acetate (100 mg, 0.188 mmol) in THF (2 mL) was added methylmagnesium bromide (0.3 mL, 3 mol/L) at −78° C. The formed mixture was stirred for 3 h. The reaction was quenched by aqueous solution of NH4Cl. The organic phase was separated and concentrated to provide the crude product, which was purified by TLC to give (R)-3-((S)-1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 10%). 1H NMR (CDCl3): δ=1.08 (d, 6H), 1.19 (m, 2H), 1.42 (d, 3H), 1.64 (m, 2H), 1.84 (m, 2H), 2.04-2.19 (m, 4H), 2.53 (s, 2H), 2.80 (m, 1H), 3.29 (t, 2H), 3.72 (s, 3H), 4.25 (s, 2H), 5.54 (q, 1H), 6.74 (m, 5H), 6.82 (m, 2H), 7.10 (m, 3H), 7.23 (m, 4H).

Workup

  1. customThe reaction was quenched by aqueous solution of NH4Cl
  2. customThe organic phase was separated
  3. concentrationconcentrated
  4. customto provide the crude product, which
  5. customwas purified by TLC

Sources & evidence

ORD record
ord-ceba5c850e4146f99b44554277104c3e
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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