2-[6-(1-Benzhydryl-3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester → HCID 86727356, compound

HRID 519001Notes

Reaction equation

HRID 519001 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH:5]([N:7]1[C:12]2[CH:13]=[C:14]([O:17][C:18]3([CH3:35])[CH2:21][N:20](C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:19]3)[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:36])[CH3:6])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:37])[CH:5]([N:7]1[C:12]2[CH:13]=[C:14]([O:17][C:18]3([CH3:35])[CH2:19][NH:20][CH2:21]3)[CH:15]=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:36])[CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 867273552-[6-(1-Benzhydryl-3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester

Product 1

HCID 86727356HCID 86727356, compoundYield 1,068.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-[6-(1-benzhydryl-3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester (0.300 g, 0.070 mmol) and Pd(OH)2/C (10%, 0.170 g) in EtOH (15 mL) was stirred under H2 (50 psi) at ambient temperature overnight. The reaction mixture was filtered and the filtrate was evaporated in vacuo to give 2-[6-(3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester (0.250 g, crude) as an oil, which was used in the next step directly. LC/MS (Table 1, Method 2) Rt=0.806 min.; MS m/z: 335 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c4ec10f503ff45e98aa513f797d957f3
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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