Trifluoroacetic acid → HCID 59540201, compound

HRID 923404Notes

Reaction equation

HRID 923404 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[CH2:66][CH2:65][CH2:64][C@H:14]1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:40](=[O:63])[C@@H:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:46](=[O:62])[C@H:47]([NH:54]C(OC(C)(C)C)=O)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:35][CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=[O:16])=[O:12])[C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([N:13]1[CH2:66][CH2:65][CH2:64][C@H:14]1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([NH:39][C:40](=[O:63])[C@@H:41]3[CH2:45][CH2:44][CH2:43][N:42]3[C:46](=[O:62])[C@H:47]([NH2:54])[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:37][CH:38]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)=[O:16])=[O:12])[C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59540248HCID 59540248, compound

Product 1

HCID 59540201HCID 59540201, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 74 (136.1 mg, 0.151 mmol) in CH2Cl2 (0.2 mL) was added trifluoroacetic acid (0.20 mL). The mixture was stirred at rt and concentrated in vacuo. The crude product was partitioned between CH2Cl2 and saturated aqueous NaHCO3, and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (115 mg, 94%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.96 (s, 8 H), 1.53 (s, 1 H), 1.74 (s, 1 H), 1.82-1.91 (m, 3 H), 1.99 (s, 2 H), 2.15 (s, 1 H), 2.69 (s, 2 H), 2.84 (s, 1 H), 3.54 (s, 3 H), 3.63 (s, 1 H), 3.79 (s, 2 H), 4.21 (d, J=8.9 Hz, 1 H), 4.41-4.47 (m, 2 H), 4.60 (s, 4 H), 5.29 (s, 1 H), 6.57 (t, J=7.2 Hz, 1 H), 6.66 (d, J=8.2 Hz, 2 H), 7.05-7.11 (m, 3 H), 7.19 (t, J=8.3 Hz, 4 H), 7.42-7.49 (m, 4 H), 7.53 (dd, J=12.8, 8.5 Hz, 5 H), 10.00 (s, 1 H), 10.09 (s, 1 H); MS (ESI) m/z 802.5 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4167a29250eb4e50af12f1c05e536f2e
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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