Trifluoroacetic acid → HCID 42600566, compound

HRID 384528Notes

Reaction equation

HRID 384528 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 42600566HCID 42600566, compoundYield 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-b3dbeaddbbff4723b484c8d2a652b102
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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