Trifluoroacetic acid → HCID 68860305, compound

HRID 1370941Notes

Reaction equation

HRID 1370941 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:51]=[CH:50][C:25]([O:26][C:27]2[CH:49]=[CH:48][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][C@H:38]([C:41]([O:43]C(C)(C)C)=[O:42])[CH2:39][OH:40])=[O:36])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]([CH2:21][C:22]1[CH:51]=[CH:50][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:37][C@H:38]([C:41]([OH:43])=[O:42])[CH2:39][OH:40])=[O:36])=[CH:48][CH:49]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68859989HCID 68859989, compound

Product 1

HCID 68860305HCID 68860305, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 258A was treated with 10% trifluoroacetic acid in dichloromethane (2 ml) for 5 hours at room temperature and concentrated in vacuo. Residue purified by HPLC to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.04-12.95 (br.s, 1 H), 8.94 (s, 1 H), 8.00 (d, 1 H), 7.24 (m, 7 H), 6.88-7.09 (m, 7 H), 6.82 (d, 2 H), 4.29 (m, 1 H), 4.05 (s, 2 H), 4.00 (s, 2 H), 3.95 (t, 2 H), 3.65 (m, 2 H), 2.91 (s, 3 H), 2.38 (s, 3 H), 2.32 (m, 2 H), 1.94 (m, 2 H); MS (ESI+) m/z 662 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customResidue purified by HPLC

Sources & evidence

ORD record
ord-b55bc2907d83435980d446ecc2907c7e
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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