HCID 178447445, compound → HCID 178464334, compound

HRID 1036527Notes

Reaction equation

HRID 1036527 reaction equation
[N+:1]([C:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:23]3)[CH:17]=2)[CH:12]=1)([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([F:29])([F:30])[F:31])[CH2:24][CH2:23]3)[CH:17]=2)[CH:12]=1)([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 178447445HCID 178447445, compound

Product 1

HCID 178464334HCID 178464334, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4-nitro-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid (0.099 g, 0.22 mmol) in acetic acid (2.00 mL, Fisher) at 20° C. was added zinc (0.185 g, 2.83 mmol, Aldrich). The mixture was stirred for 45 minutes at room temperature. The mixture was heated at 50° C. and stirred. After 2.5 h, the mixture was diluted in acetic acid, filtered and concentrated to dryness under reduced pressure. Purification was by preparative HPLC. The fractions were dried to give 61 mg (52%) product as TFA salt. MS: m/z=432.10 [M+Na]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 7.62-7.74 (m, 3H), 7.36 (dd, J=8.8, 1.8 Hz, 1H), 7.03-7.12 (m, 2H), 4.21-4.32 (m, 1H), 2.20-2.41 (m, 4H), 1.91-2.19 (m, 5H), 1.72 (s, 3H), 1.35-1.51 (m, 4H).

Workup

  1. temperatureThe mixture was heated at 50° C.
  2. stirringstirred
  3. waitAfter 2.5 h
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification
  7. customThe fractions were dried

Sources & evidence

ORD record
ord-2ff9bf3ff857425a87fb7ba340404cc8
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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