Trifluoroacetic acid → 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoic Acid

HRID 1860679Notes

Reaction equation

HRID 1860679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([O:25]CC)=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.FC(F)(F)C(O)=O>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([CH3:29])([CH3:28])[CH2:22][C:23]([OH:25])=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 12018742Ethyl 4-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate

Product 1

HCID 101098274-{3-methoxy-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product of STEP 8 (67.5 mg, 0.17 mmol) was dissolved in 5 ml methanol and 5 ml 1N sodium hydroxide solution. The reaction was stirred at room temperature for 16 h, and acidified with trifluoroacetic acid (1.0 ml). Solvents were evaporated and residue was purified on HPLC using acetonitrile gradient 10-50% in 30 min to yield 31.5 mg. FAB-MS: (MH+)=373. H NMR(CDCl3) δ1.03 (s, 6H), 2.21 (p, 2H), 2.22 (s, 2H), 2.61 (s, 2H), 3.60 (q, 2H), 3.84 (s, 2H), 4.13 (t, 2H), 6.65-6.82 (m, 4H), 6.96 (d, 1H), 7.68-7.80 (m, 2H); Anal Calcd. for C21H28N2O4 plus 1.5 CF3COOH: C, 52.17; H, 5.56; N, 5.07. Found: C, 52.44; H, 5.62; N, 4.88.

Workup

  1. customSolvents were evaporated
  2. customresidue was purified on HPLC
  3. customin 30 min
  4. customto yield 31.5 mg

Sources & evidence

ORD record
ord-f8b2596801664b6dbf0ab6e542a0bf00
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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