Trifluoroacetic acid → Trifluoroacetic acid

HRID 1755452Notes

Reaction equation

HRID 1755452 reaction equation
[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8](=[O:18])[CH2:9][NH:10]C(=O)OC(C)(C)C)[C@@H:3]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(Cl)Cl>[NH2:10][CH2:9][C:8]([N:4]1[CH2:5][C@H:6]([OH:7])[C@@H:2]([OH:1])[C@H:3]1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:18].[C:30]([OH:32])([C:29]([F:34])([F:33])[F:28])=[O:31]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86700100tert-Butyl 2-((2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidin-1-yl)-2-oxoethylcarbamate

Product 2

HCID 6422Trifluoroacetic acidHCID 867001012-Amino-1-((2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 11, except using material from Example 40 (350 mg, 0,920 mmol), CH2Cl2 (35 mL, trifluoroacetic acid (500 μlit, 6.49 mmol) and stirring at room temp for 45 min, the title compound is isolated (quantitative yield) as a mono TFA salt and is used crude, “as is”, in the next step. LC/MS (Condition A): ret. T=1.54 min, (M+H)+ 281.19.

Sources & evidence

ORD record
ord-12447b39c970497aa9aef16c07d6ea83
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

Loading…