Trifluoroacetic acid → 2-Amino-1-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-3-(4-methoxyphenyl)propan-1-one trifluoroacetate

HRID 530700Notes

Reaction equation

HRID 530700 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])[CH2:17][N:16]([C:18](=[O:37])[C@H:19]([NH:29]C(=O)OC(C)(C)C)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>ClCCl>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[NH2:29][CH:19]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:18]([N:16]1[CH2:17][C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])[CH2:15]1)=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729201tert-butyl [(R)-2-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-1-(4-methoxybenzyl)-2-oxoethyl]carbamate

Product 1

HCID 711521902-Amino-1-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-3-(4-methoxyphenyl)propan-1-one trifluoroacetateYield 120.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.14 g (1.89 mmol) of tert-butyl [(R)-2-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-1-(4-methoxybenzyl)-2-oxoethyl]carbamate are dissolved in 10 ml of dichloromethane. 3 ml (39 mmol) of trifluoroacetic acid are added dropwise and the mixture is stirred at room temperature for 1 hour and then concentrated to dryness. 1.4 g of 2-amino-1-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-3-(4-methoxyphenyl)propan-1-one trifluoroacetate are obtained in the form of a colourless resin, in quantitative yield.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3c17784ff7464883a3253a95e23b0dd0
Source dataset
uspto-grants-2016_05
Patent number
US09353083B2

Reaction notes

Loading…