Trifluoroacetic acid methylene chloride → HCID 58466535, compound

HRID 1968889Notes

Reaction equation

HRID 1968889 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]2[CH2:38][CH2:37][CH2:36]2)=[CH:29][CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16])[C@@H:9]([CH3:12])[CH2:10][CH3:11])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[NH2:7][C@@H:8]([C@@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:13][N:14]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH:35]2[CH2:38][CH2:37][CH2:36]2)=[CH:29][CH:28]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=1)=[O:16]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67436440HCID 67436440, compound

Product 1

HCID 58466535HCID 58466535, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(1S,2S)-1-({(4-cyclobutylmethoxy-phenyl)-[(1R,2R)-2-(5-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-amino}-methyl)-2-methyl-butyl]-carbamic acid tert-butyl ester (53 mg) in DCM (1 mL) was treated with TFA/DCM (1/1 mL) for 1 h. The mixture was concentrated to give the titled compound as di-TFA salts (60.7 mg). 1H NMR (400 MHz, MeOD) δ ppm 8.2 (d, J=3.0 Hz, 1H), 7.5 (td, J=8.5, 2.9 Hz, 1H), 7.3 (dd, J=8.8, 4.3 Hz, 1H), 7.3 (d, J=8.1 Hz, 2H), 6.9 (d, J=8.3 Hz, 2H), 4.3 (dd, J=14.9, 8.8 Hz, 1H), 3.9 (dd, J=6.6, 2.3 Hz, 2H), 3.6 (dd, J=14.9, 2.8 Hz, 1H), 3.3-3.4 (m, 1H), 2.8 (dt, J=14.6, 7.2 Hz, 1H), 2.6 (dd, J=6.3, 2.5 Hz, 1H), 2.1 (td, J=8.5, 5.6 Hz, 2H), 1.8-2.1 (m, 5H), 1.8 (ddd, J=7.7, 5.9, 1.5 Hz, 1H), 1.7 (ddd, J=9.0, 5.4, 3.8 Hz, 1H), 1.4 (ddd, J=8.5, 6.0, 3.9 Hz, 1H), 1.4 (dd, J=7.5, 5.7 Hz, 1H), 1.2 (dd, J=15.5, 5.4 Hz, 1H), 1.0 (d, J=6.8 Hz, 3H), 0.9 (t, 3H). LRMS (ESI)=440.3, [(M+H)+, Calcd for C26H35FN3O2 439.6].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-39affa37a9584bd6875d7ad485457df2
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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