Trifluoroacetic acid → HCID 58760126, compound

HRID 857740Notes

Reaction equation

HRID 857740 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13](=[O:45])[CH2:14][NH:15][C@H:16]([CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[C:17]([N:19]1[CH2:22][CH2:21][C@H:20]1[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1[N:34]1[CH:38]=[N:37][CH:36]=[N:35]1)=[O:24])=[O:18])(C)(C)C>C(Cl)Cl>[Cl:33][C:31]1[CH:30]=[CH:29][C:28]([N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)=[C:27]([CH:32]=1)[CH2:26][NH:25][C:23]([C@@H:20]1[CH2:21][CH2:22][N:19]1[C:17](=[O:18])[C@H:16]([NH:15][CH2:14][C:13]([OH:45])=[O:12])[CH:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131726159HCID 131726159, compound

Product 1

HCID 58760126HCID 58760126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (5 mL) was added to a solution of tert-butyl({(1R)-2-[(2S)-2-({[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]amino}carbonyl)azetidin-1-yl]-1-cyclohexyl-2-oxoethyl}amino)acetate (22 mg, 0.04 mmol) in CH2Cl2 (5 mL) at 0° C. After stirring for 16 h the reaction mixture was concentrated. The title compound was isolated by reverse phase HPLC. LCMS (M+H): 489.3. 1H NMR (400 MHz, CD3OD): δ 8.80 (s, 1H), 8.22 (s, 1H), 7.67 s, 1H), 7.50 (m, 2H), 4.79 (m, 1H), 4.45–4.20 (m, 5H), 3.91 (m, 3H), 2.61 (m, 1H), 2.21 (m, 1H), 1.87–1.72 (m, 5H), 1.37–1.17 (m, 5H).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-c64abed4ac5e4f508e5d16d0d90e0f23
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…