HCID 86727396, compound → HCID 86727398, compound

HRID 519035Notes

Reaction equation

HRID 519035 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([CH3:30])=[CH2:29])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:32])[C:19](=[O:31])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[CH:28]([CH3:29])[CH3:30])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:32])[C:19](=[O:31])[NH:20][N:21]=2)([CH3:12])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86727396HCID 86727396, compound

Product 1

HCID 86727398HCID 86727398, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-(7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.054 g, 0.122 mmol) and Pd/C (10%, 0.015 g) in MeOH (10 mL) was stirred under H2 (50 psi) at ambient temperature overnight. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether) to give 3-(7-isopropyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester as a white solid (0.049 g, 95%). LC/MS (Table 1, Method 2) Rt=1.327 min.; MS m/z: 467 [M+23]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-17149e991ebc431ab0bc9f1bff4d9ef4
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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