Trifluoroacetic acid → HCID 69219055, compound

HRID 272737Notes

Reaction equation

HRID 272737 reaction equation
CC1(C)[O:6][C@H:5]2[C:7](=[O:51])[O:8][C@H:9]([CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[CH:20][C:21]5[C:27](=[O:28])[NH:26][C:25]6[CH:29]=[C:30]([CH2:33][CH2:34][O:35][C:36]7[CH:41]=[CH:40][C:39]([N:42]8[CH2:47][CH2:46][O:45][CH2:44][CH2:43]8)=[CH:38][CH:37]=7)[CH:31]=[CH:32][C:24]=6[NH:23][C:22]=5[CH:48]=4)=[CH:14][C:13]=3[O:49][CH3:50])[C@H:4]2[O:3]1.FC(F)(F)C(O)=O>ClCCl>[OH:3][C@H:4]1[C@@H:5]([OH:6])[C:7](=[O:51])[O:8][C@@H:9]1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]3[C:27](=[O:28])[NH:26][C:25]4[CH:29]=[C:30]([CH2:33][CH2:34][O:35][C:36]5[CH:41]=[CH:40][C:39]([N:42]6[CH2:43][CH2:44][O:45][CH2:46][CH2:47]6)=[CH:38][CH:37]=5)[CH:31]=[CH:32][C:24]=4[NH:23][C:22]=3[CH:48]=2)=[CH:14][C:13]=1[O:49][CH3:50]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69216852HCID 69216852, compound

Product 1

HCID 69219055HCID 69219055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 642B (11.2 mg, 0.016 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (50 μL, 0.65 mmol) and stirred at room temperature. The reaction mixture was then concentrated and purified by preparative HPLC. MS (ESI) m/e 668 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 9.74 (s, 1H), 7.84 (s, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.25 (d, J=1.5 Hz, 1H), 7.22 (d, J=1.8 Hz, 1H), 7.15-1.19 (m, 2H), 7.07 (d, J=8.3 Hz, 1H), 6.85-6.96 (m, 7H), 4.73 (d, J=5.5 Hz, 1H), 4.59 (t, J=3.4 Hz, 1H), 4.25-4.29 (m, 3H), 4.05 (t, J=6.8 Hz, 2H), 3.86 (s, 3H), 3.75-3.85 (m, 2H), 3.73-3.75 (m, 4H), 3.03-3.05 (m, 4H), 2.87 (t, J=6.6 Hz, 2H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-38a9bcdef83847a0acf47dbc8bdb403f
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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