Trifluoroacetic acid → Ammonia

HRID 2060802Notes

Reaction equation

HRID 2060802 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[C:13]([C@:17]34[CH2:26][CH2:25][O:24][CH2:23][CH:22]3[CH2:21][S:20][C:19]([NH:27]C(=O)OC(C)(C)C)=[N:18]4)[CH:14]=[CH:15][CH:16]=2)=[O:9])=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:6].[ClH:1].[ClH:1].[NH2:27][C:19]1[S:20][CH2:21][CH:22]2[CH2:23][O:24][CH2:25][CH2:26][C@:17]2([C:13]2[CH:12]=[C:11]([NH:10][C:8](=[O:9])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[CH:16]=[CH:15][CH:14]=2)[N:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66861615HCID 66861615, compound

Product 2

HCID 222AmmoniaHCID 57504928HCID 57504928, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (8aS)-8a-(3-(5-chloropicolinamido)phenyl)-4,4a,5,7,8,8a-hexahydropyrano[4,3-d][1,3]thiazin-2-ylcarbamate (0.172 g, 0.342 mmol) in CH2Cl2 (8 mL) is added TFA (4 mL) and the reaction is stirred at room temperature for 1 hour. The solvent is removed under reduced pressure. The residue is purified on a 10 g SCX column using 4:1 CH2Cl2:MeOH followed by 2:1 CH2Cl2: 7 N NH3 in MeOH to afford the title compound as a freebase (0.127 g, 92%). The freebase (0.124 g, 0.308 mmol) is dissolved in CH2Cl2 and treated with 1 M HCl in Et2O (0.65 mL, 0.605 mmol) and the solvent is removed under reduced pressure to afford the title compound (0.127 g, 78%). ES/MS m/e (35Cl/37Cl) 403, 405 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is purified on a 10 g SCX column

Sources & evidence

ORD record
ord-9f982d161e7c4560b33b94567ab78133
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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