Trifluoroacetic acid → N-[(4aR,7aS)-7a-(3-Aminophenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 77579Notes

Reaction equation

HRID 77579 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[C:11]([C@:15]23[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][C@H:20]2[CH2:19][S:18][C:17]([NH:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:16]3)[CH:12]=[CH:13][CH:14]=1>ClCCl>[NH3:8].[NH2:8][C:9]1[CH:10]=[C:11]([C@:15]23[CH2:23][NH:22][CH2:21][C@H:20]2[CH2:19][S:18][C:17]([NH:31][C:32](=[O:39])[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:16]3)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762764tert-butyl (4aR,7aS)-7a-(3-aminophenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 2

HCID 222AmmoniaHCID 86762765N-[(4aR,7aS)-7a-(3-Aminophenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideYield 159.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25 mL) is added to a solution of tert-butyl (4aR,7aS)-7a-(3-aminophenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (4 g, 8.84 mmol) in dichloromethane (100 mL) and the mixture is stirred at room temperature under nitrogen for 4 hours. The solvent is removed in vacuo and the crude product is purified with an SCX column using 3:1 dichloromethane:methanol and then 2:1 dichloromethane:7 N ammonia in methanol to give the title compound (2.49 g, 80%). ES/MS (m/e): 353 (M+H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified with an SCX column

Sources & evidence

ORD record
ord-0b72c1a008564bdb9254d71f4944088c
Source dataset
uspto-grants-2014_09
Patent number
US08841293B1

Reaction notes

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