Formaldehyde → Ethyl N-{4-[{3-([tert-butoxycarbonyl)(methyl)amino]propyl}(methyl)carbamoyl]phenyl}-N-methyl-beta-alaninate

HRID 446607Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

The compound (239 mg, 0.57 mmol) obtained in Example 94a was dissolved in methanol (15 mL), paraformaldehyde (179 mg, 5.67 mmol) and 10% palladium-carbon (48 mg, 20% by weight) were added, and the mixture was stirred at 60° C. under a hydrogen atmosphere for 18 hours. After the reaction was completed, the reaction mixture was filtered through celite, the filtrate was washed with methanol, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate, 10:1, v/v) to give the title compound (172 mg; yield, 70%) as a pale pink oily substance.

Workup

filtrationthe reaction mixture was filtered through celite
washthe filtrate was washed with methanol
customthe solvent was evaporated under reduced pressure
customThe residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record: ord-3f9ad82c73374e57b91b2975f477cdd4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476253B2

Reaction notes

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