Trifluoroacetic acid → HCID 136337592, compound

HRID 494640Notes

Reaction equation

HRID 494640 reaction equation
[CH:1]1([CH2:4][C:5]2([CH3:37])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([OH:15])=[C:7]([C:16]3[NH:21][C:20]4[CH:22]=[CH:23][C:24]([NH:26]C(=O)OC(C)(C)C)=[CH:25][C:19]=4[S:18](=[O:35])(=[O:34])[N:17]=3)[C:6]2=[O:36])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[NH2:26][C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:16]([C:7]3[C:6](=[O:36])[C:5]([CH2:4][CH:1]4[CH2:2][CH2:3]4)([CH3:37])[C:14]4[C:9]([C:8]=3[OH:15])=[CH:10][CH:11]=[CH:12][CH:13]=4)=[N:17][S:18](=[O:35])(=[O:34])[C:19]=2[CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136384670HCID 136384670, compound

Product 1

HCID 136337592HCID 136337592, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 164D (0.100 g, 0.1912 mmol) in dichloromethane (4 mL) was treated with trifluoroacetic acid (4 mL) at room temperature for 1 hour. After concentrating in. vacuo, the resulting oil was partitioned between ethyl acetate and aqueous NaHCO3, 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.

Workup

  1. concentrationAfter concentrating in
  2. customvacuo, the resulting oil was partitioned between ethyl acetate and aqueous NaHCO3
  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. customvacuo to yield a solid that
  9. customwas used without further purification

Sources & evidence

ORD record
ord-a575be3d64bf4e4683d68aae02af95f8
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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