Tert-butyl(+/-)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate → tert-Butyl(+/-)-3-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]acetyl}amino)-2-methylphenyl]propanoate

HRID 877190Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[C:13]([NH:15][C:16]2[C:17]([CH3:31])=[C:18]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:19]=[CH:20][CH:21]=2)=[O:14])=[CH:8][CH:7]=1)(=O)C>N.CO>[CH:32]1([CH:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[CH:7][CH:8]=2)[C:13]([NH:15][C:16]2[C:17]([CH3:31])=[C:18]([CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:19]=[CH:20][CH:21]=2)=[O:14])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 35 °C

Procedure

16.0 g (32.41 mmol) of tert-butyl(+/−)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate were dissolved in 300 ml of a 2 M solution of ammonia in methanol and initially stirred at 30-40° C. for 2 h and then overnight at RT. The solution was then concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase dichloromethane/methanol 100:1). This gave 13.6 g (93.1% of theory) of the title compound.

Workup

customovernight
customat RT
concentrationThe solution was then concentrated under reduced pressure
customthe residue was purified by chromatography on silica gel (mobile phase dichloromethane/methanol 100:1)

Sources & evidence

ORD record: ord-ba0cebb5bb914556b274ee72d473c527
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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