Trifluoroacetic acid → 5-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

HRID 545620Notes

Reaction equation

HRID 545620 reaction equation
C(OC([CH:8]1[CH:12]2[CH2:13][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[S:25][C:26]5[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=5[N:28]=4)=[CH:19][CH:18]=3)[CH2:15][CH:11]2[CH2:10][N:9]1[S:33]([NH2:36])(=[O:35])=[O:34])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CO.CS(C)=O>[S:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:14]2[CH2:15][CH:11]3[CH2:10][N:9]([S:33]([NH2:36])(=[O:34])=[O:35])[CH2:8][CH:12]3[CH2:13]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86629966Tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide

Product 1

HCID 426005665-[4-(Benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amideYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

To a stirred solution tert-butoxy carbonyl-5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-sulfonic acid amide (108 mg, 0.20 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (1 mL). The homogeneous reaction mixture was allowed to stir overnight at rt. The crude reaction mixture was blown down to dryness and dissolved in CH3OH/DMSO (2:1) and purified via reverse phase preparative HPLC to afford the title compound as fluffy white powder (60 mg, 70%). MS (ESI): mass calcd. for C20H22N4O3S2, 430.6; m/z found, 431.1 [M+H]+; 1H NMR (500 MHz, CD3OD): 7.79 (d, J=8.0 Hz, 1H), 7.67 (d, J=8.1 Hz, 1H), 7.52-7.46 (m, 2H), 7.46-7.39 (m, 1H), 7.37-7.27 (m, 3H), 3.68 (s, 2H), 3.24 (dd, J=9.5, 7.0 Hz, 2H), 3.06 (dd, J=9.4, 2.6 Hz, 2H), 2.93-2.87 (m, 2H), 2.87-2.78 (m, 2H), 2.40 (dd, J=8.5, 3.6 Hz, 2H).

Workup

  1. customThe crude reaction mixture
  2. custompurified via reverse phase preparative HPLC

Sources & evidence

ORD record
ord-90f5b99246c24c5097d7e4216b33fbd1
Source dataset
uspto-grants-2011_05
Patent number
US07935725B2

Reaction notes

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