Sodium Hydroxide → 3-[2-(4-Benzyloxy-phenyl)-5-oxo-morpholin-4-yl]-propionic acid tert-butyl ester

HRID 920559Notes

Reaction equation

HRID 920559 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][NH:19][C:18](=[O:21])[CH2:17][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH:25]=[CH2:26]>C1COCC1>[C:29]([O:28][C:24](=[O:27])[CH2:25][CH2:26][N:19]1[C:18](=[O:21])[CH2:17][O:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[CH2:20]1)([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15458tert-Butyl acrylateHCID 666539576-(4-(Benzyloxy)phenyl)morpholin-3-one

Product 1

HCID 666540583-[2-(4-Benzyloxy-phenyl)-5-oxo-morpholin-4-yl]-propionic acid tert-butyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-(4-benzyloxy-phenyl)-morpholin-3-one (13.40 g; 47.3 mmol) and powdered NaOH (3.78 g; 94.6 mmol) in THF (250 mL) was added tert-butyl acrylate (13.7 mL; 94.6 mmol). The resulting mixture was stirred at RT for 2 hours and subsequently concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O) to afford 3-[2-(4-benzyloxy-phenyl)-5-oxo-morpholin-4-yl]-propionic acid tert-butyl ester (14.20 g).

Workup

  1. concentrationsubsequently concentrated in vacuo
  2. customThe residue was purified by column chromatography (SiO2, Et2O)

Sources & evidence

ORD record
ord-f10f7d60a4bd46eb90a7b0ee5eb4141b
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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