(+/-)-Tert-butyl 1-[3-({[4-(acetoxymethyl)phenyl](cyclopentyl)acetyl}-amino)benzyl]cyclopropanecarboxylate → (+/-)-Tert-butyl 1-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]-acetyl}amino)benzyl]cyclopropanecarboxylate

HRID 1475654Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:13]([NH:15][C:16]2[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[CH2:19][C:20]2([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[O:14])=[CH:8][CH:7]=1)(=O)C>N.CO>[CH:33]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[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[CH2:19][C:20]2([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:22][CH2:21]2)=[O:14])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Conditions

Temperature: 30 °C

Procedure

12.50 g (24.72 mmol) of (+/−)-tert-butyl 1-[3-({[4-(acetoxymethyl)phenyl](cyclopentyl)acetyl}-amino)benzyl]cyclopropanecarboxylate were dissolved in 228 ml of a 2 M solution of ammonia in methanol and stirred at 30° C. for 2 h, then at 40° C. for 2 h and finally at RT overnight. The solution was then concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1). This gave 11.88 g (96.5% of theory) of the target compound.

Workup

waitat 40° C. for 2 h
customfinally at RT
customovernight
concentrationThe solution was then concentrated under reduced pressure
customthe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1)

Sources & evidence

ORD record: ord-cf1887b53e324f468a5bda459b96d96c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018258B2

Reaction notes

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