Ammonia → HCID 68176356, compound

HRID 408604Notes

Reaction equation

C(O[C:4](=[O:35])[CH2:5][CH2:6][CH2:7][N:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:9]([C:11]1([CH3:26])[CH2:14][CH2:13][N:12]1[C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[O:10])C.[NH3:36]>CO>[C:4]([CH2:5][CH2:6][CH2:7][N:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:9]([C:11]1([CH3:26])[CH2:14][CH2:13][N:12]1[C:15](=[O:25])[CH2:16][C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[O:10])(=[O:35])[NH2:36]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-((4-chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-butyric acid ethyl ester, Intermediate 146 (1 eq.) in MeOH was added an aqueous solution of NH3 (20% in water). The reaction was stirred at 60° C. for 15 h then cooled to 20° C. The solvents were evaporated under reduced pressure and the crude was purified by preparative LCMS to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (3-carbamoyl-propyl)-(4-chloro-benzyl)-amide.

Workup

temperaturethen cooled to 20° C
customThe solvents were evaporated under reduced pressure
customthe crude was purified by preparative LCMS

Sources & evidence

ORD record: ord-a0011fec58704b86bbada38f15014002
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

Loading…