HCID 58109684, compound → HCID 58109426, compound

HRID 2037563Notes

Reaction equation

HRID 2037563 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([N:12]2[CH2:17][CH2:16][C@:15]([CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][C:13]2=[O:37])[CH3:11])=[CH:6][CH:5]=1.CC(C)=[O:40].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][O:27][CH2:26][CH2:25][CH2:24][C@@:15]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][C:13](=[O:37])[N:12]([C@H:10]([C:7]3[CH:8]=[CH:9][C:4]([CH2:3][C:2]([OH:40])=[O:1])=[CH:5][CH:6]=3)[CH3:11])[CH2:17][CH2:16]2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 58109684HCID 58109684, compoundHCID 131709961Jones' reagent

Product 1

HCID 58109426HCID 58109426, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-3-((S)-1-(4-(2-hydroxyethyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (260 mg, 0.517 mmol) in acetone (2 mL) was added Jones reagent (0.25 mL, 2.5 mol/L), and the formed mixture was stirred for 30 min. The mixture was extracted with EtOAc. The combined organic layer was concentrated to give crude 2-(4-((S)-1-((R)-6-(3-(4-methoxybenzyloxy)propyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)acetic acid (260 mg, 97%), which was used for the next step without purification.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. concentrationThe combined organic layer was concentrated

Sources & evidence

ORD record
ord-85efb616003d45c181212b37fac7559c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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