Trifluoroacetic acid → Ammonia

HRID 1593957Notes

Reaction equation

HRID 1593957 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[CH:8][C:9]([N:12]3[CH2:17][C@@H:16]4[CH2:18][C@H:13]3[CH2:14][N:15]4C([O:21][C:22]([CH3:25])(C)C)=O)=[N:10][CH:11]=2)=[CH:2]1.F[C:27](F)(F)[C:28]([OH:30])=[O:29].[OH-:33].[Na+]>>[NH3:7].[C:28]([OH:30])(=[O:29])/[CH:27]=[CH:25]/[C:22]([OH:21])=[O:33].[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[CH:8][C:9]([N:12]3[CH2:17][C@@H:16]4[CH2:18][C@H:13]3[CH2:14][NH:15]4)=[N:10][CH:11]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69413856HCID 69413856, compound

Product 2

HCID 222AmmoniaHCID 131726691HCID 131726691, compound

Procedure

A mixture of 2-[5-(3-thienyl)-2-pyrazinyl]-(1S,4S)-5-tert-butoxycarbonyl-2,5-diazabicyclo-[2.2.1]-heptane (1.4 g, 3.9 mmol), triflouroacetic acid (4.4 g, 39 mmol) was stirred for 15 hours. Aqueous sodium hydroxide (50 ml, 1 M) was added and the mixture was extracted with dichloromethane (2×30 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.41 g (28%), Mp 208.4-208.9° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×30 ml)

Sources & evidence

ORD record
ord-82a4266fd52f41e7b2a5aa97cd11ff6f
Source dataset
uspto-grants-2007_11
Patent number
US07300933B2

Reaction notes

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