Trifluoroacetic acid → 3,N-Dihydroxy-2,2-dimethyl-3-[6-(2-methyl-quinolin-4-ylmethoxy)-naphthalen-2-yl]-propionamide

HRID 2212571Notes

Reaction equation

HRID 2212571 reaction equation
C(O[C:4](=[O:33])[C:5]([CH3:32])([CH3:31])[CH:6]([OH:30])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)[CH:13]=2)[CH:8]=1)C.C[O-].[Na+].Cl.[OH:38][NH2:39].CO.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>>[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].[OH:30][CH:6]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)[CH:13]=2)[CH:8]=1)[C:5]([CH3:31])([CH3:32])[C:4]([NH:39][OH:38])=[O:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 695963243-Hydroxy-2,2-dimethyl-3-[6-(2-methyl-quinolin-4-ylmethoxy)-naphthalen-2-yl]-propionic acid ethyl esterHCID 86592943sodium methoxide hydroxyl amine HCl methanol

Product 2

HCID 6422Trifluoroacetic acidHCID 104553663,N-Dihydroxy-2,2-dimethyl-3-[6-(2-methyl-quinolin-4-ylmethoxy)-naphthalen-2-yl]-propionamideYield 59%

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-2,2-dimethyl-3-[6-(2-methyl-quinolin-4-ylmethoxy)-naphthalen-2-yl]-propionic acid ethyl ester (1.35 g, 3.04 mmol) was added portion wise to a 50° C. solution of sodium methoxide/hydroxyl amine HCl/methanol ˜1.34 M (230 mL, 308 mmol) under nitrogen atmosphere. The reaction was stirred for 0.5 h, cooled to 0° C., made neutral with TFA, and concentrated in vacuo. The residue was taken up in water (800 mL) and the pH adjusted to 2–3 with TFA to give a solid precipitate. The product was purified by HPLC on a C-18 column eluting with an acetonitrile:water:TFA gradient to give the title compound (0.98 g, 59%) as a white solid. MS found: (M+H)+=431.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a solid precipitate
  3. customThe product was purified by HPLC on a C-18 column
  4. washeluting with an acetonitrile

Sources & evidence

ORD record
ord-d46bc409b0c24067a61c8a40d3e2cbf0
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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