HCID 86727386, compound → HCID 86727388, compound

HRID 519027Notes

Reaction equation

HRID 519027 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([N:7]1[C:12]2[CH:13]=[C:14]([O:18][C:19]3([CH3:36])[CH2:22][N:21](C(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:20]3)[C:15]([F:17])=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:37])[CH3:6])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:38])[CH:5]([N:7]1[C:12]2[CH:13]=[C:14]([O:18][C:19]3([CH3:36])[CH2:20][NH:21][CH2:22]3)[C:15]([F:17])=[CH:16][C:11]=2[O:10][CH2:9][C:8]1=[O:37])[CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 86727386HCID 86727386, compound

Product 1

HCID 86727388HCID 86727388, compoundYield 144.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-[7-fluoro-6-(1-benzhydryl-3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester (0.280 g, 0.540 mmol) and Pd(OH)2/C (10%, 0.140 g, 0.1 mmol) 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-[7-fluoro-6-(3-methyl-azetidin-3-yloxy)-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl]-propionic acid ethyl ester (0.275 g, crude) as an oil, which was used in the next step directly. LC/MS (Table 1, Method 3) Rt=1.026 min.; MS m/z: 353 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-fa88de7bdca44c63b5cf75538217d1ae
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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