Trifluoroacetic acid → (R)-2-Amino-3-(4-methoxyphenyl)-1-(3-pentyloxy-3-o-tolylazetidin-1-yl)propan-1-one trifluoroacetate

HRID 540377Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:9](=[O:27])[N:10]1[CH2:13][C:12]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:11]1)(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>ClCCl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH2:7][C@H:8]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[C:9]([N:10]1[CH2:11][C:12]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:13]1)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

2.81 g (5.5 mmol) of tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamate are solubilized in 10 ml of dichloromethane. The reaction medium is cooled to 0° C. 6.5 ml of trifluoroacetic acid are then introduced. After a return to ambient temperature, the reaction medium is stirred for 5 hours and then concentrated to dryness. The crude product obtained is purified by silica gel chromatography (eluent 9/1 dichloromethane/methanol). 2.81 g in the form of a white powder are obtained with a yield of 97%.

Workup

concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-efa0829eb7bb4203a744c14fda4610c0
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871187B2

Reaction notes

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