Trifluoroacetic acid → HCID 67206043, compound

HRID 1799063Notes

Reaction equation

HRID 1799063 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[N:29]=2)=[CH:20][CH:19]=1)=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]2[S:26][C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=3[N:29]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67205672HCID 67205672, compound

Product 1

HCID 67206043HCID 67206043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S,S)-5-{2-[4-(benzothiazol-2-yloxy)-phenoxy]-ethyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.7 g, 3.6 mmol) in CH2Cl2 (15 mL) was added trifluoroacetic acid (5 mL, 65 mmol). The resulting solution was stirred at rt for 8.5 h. The solution was concentrated to provide the title compound as an oil and used as a crude compound. MS (ESI): mass calcd. for C20H21N3O2S, 367.14; m/z found, 368.2 [M+H]+. 1H NMR (400 MHz, CDCl3, mixture of rotamers): 7.73 (d, J=7.9 Hz, 1H), 7.65 (d, J=7.9 Hz, 1H), 7.38 (t, J=7.7 Hz, 1H), 7.29-7.23 (m, 3H), 6.99-6.91 (m, 2H), 4.13-4.01 (m, 2H), 3.56-3.39 (m, 2H), 3.35-3.32 (m, 1H), 3.20 (d, J=10.4 Hz, 0.5H), 3.09 (dd, J=9.7, 2.4 Hz, 0.5H), 3.06-2.82 (m, 3.5H), 2.76-2.67 (m, 1H), 2.50 (dd, J=9.6, 1.1 Hz, 0.5H), 1.88-1.57 (m, 2H).

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-66faff9dd17f4e7a8b02e70ee77a5c0f
Source dataset
uspto-grants-2013_01
Patent number
US08344008B2

Reaction notes

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