HCID 69018590, compound → HCID 57976116, compound

HRID 1865192Notes

Reaction equation

HRID 1865192 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:13]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[C:15]([O:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][O:31][CH3:32])[CH2:25][CH2:24]2)[N:14]=1)C(OC(C)(C)C)=O)[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][C:13]1[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]([O:22][CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][CH2:30][O:31][CH3:32])[CH2:27][CH2:28]2)[N:14]=1)[CH3:2]

Participants

3

Reactant 1

HCID 69018590HCID 69018590, compound

Product 1

HCID 57976116HCID 57976116, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 3 (0.856 mmol) in TFA (15 mL) was agitated at room temperature for 20 min. LCMS indicated a mixture of ˜1:1 of the tButyl cleavage/decarboxylation to tButyl and Ethyl cleavage/decarboxylation. The TFA was removed in vacuo. The resulting oil was put up in ethyl acetate and washed with sodium bicarbonate (aq., satd.), brine then dried over MgSO4 and concentrated in vacuo. The free based material (4) was dissolved in ethanol (20 mL) and hydrogenated in the presence of 10% Pd/C (30 mg) at 20 psi on the Parr shaker for 1 hour. The suspension was filtered over celite and concentrated in vacuo yielding an orange-yellow oil (253 mg, 87.4%).

Workup

  1. additiona mixture of ˜1:1 of the tButyl cleavage/decarboxylation
  2. customThe TFA was removed in vacuo
  3. washwashed with sodium bicarbonate (aq., satd.), brine
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionwas dissolved in ethanol (20 mL) and hydrogenated in the presence of 10% Pd/C (30 mg) at 20 psi on the Parr shaker for 1 hour
  7. filtrationThe suspension was filtered over celite and
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48b306552a2847d99461306ab7c33890
Source dataset
uspto-grants-2009_12
Patent number
US07626031B2

Reaction notes

Loading…