Trifluoroacetic acid → HCID 135430175, compound

HRID 2224924Notes

Reaction equation

HRID 2224924 reaction equation
[CH:1]1([CH2:5][C:6]2([CH3:38])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([NH:27]C(=O)OC(C)(C)C)=[CH:26][C:20]=4[S:19](=[O:36])(=[O:35])[N:18]=3)[C:7]2=[O:37])[CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH2:27][C:25]1[CH:24]=[CH:23][C:21]2[NH:22][C:17]([C:8]3[C:7](=[O:37])[C:6]([CH2:5][CH:1]4[CH2:4][CH2:3][CH2:2]4)([CH3:38])[C:15]4[C:10]([C:9]=3[OH:16])=[CH:11][CH:12]=[CH:13][CH:14]=4)=[N:18][S:19](=[O:36])(=[O:35])[C:20]=2[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136384847HCID 136384847, compound

Product 1

HCID 135430175HCID 135430175, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 55H (0.105 g, 0.195 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (2 mL) at room temperature for 1 hour. After concentrating in. vacuo, the resulting oil was partitioned between ethyl acetate and NaHCO3(aq), the organic layer was removed and the bicarb layer extracted 3× with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in. vacuo. to yield a solid that was used without further purification. 1H NMR (300 MHz, DMSO-d6): δ ppm 1.22 m, 3 H) 1.47 m, 3 H) 1.57 (s, 3 H) 1.71 m, 2 H) 2.18 m, 1 H) 2.32 (m, 1 H) 7.01 (m, 2 H) 7.45 (d, J=8.46 Hz, 1 H) 7.54 (t, J=7.17 Hz, 1 H) 7.76 m, 2 H) 8.15 (d, J=7.72 Hz, 1 H) 13.54 m, 1 H). MS (ESI+) m/z=438 (M+H)+.

Workup

  1. concentrationAfter concentrating in
  2. customvacuo, the resulting oil was partitioned between ethyl acetate and NaHCO3(aq)
  3. customthe organic layer was removed
  4. extractionthe bicarb layer extracted 3× with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in
  8. customto yield a solid that
  9. customwas used without further purification

Sources & evidence

ORD record
ord-0b66a18f8854457cb194a0023b5ddf46
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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