Acetic Acid → HCID 178445779, compound

HRID 1036467Notes

Reaction equation

HRID 1036467 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:31]([F:34])([F:33])[F:32])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH:22]([N+:28]([O-])=O)[CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C>[Zn]>[NH2:28][CH:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]3)[C:13]=2[C:31]([F:33])([F:34])[F:32])[CH:18]=1)[CH2:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178445744HCID 178445744, compound

Product 1

HCID 178445779HCID 178445779, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Zinc (0.194 g, 2.96 mmol) was added to a solution of 4-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-4-nitro-butyric acid (0.102 g, 0.212 mmol) in acetic acid (3.00 mL, 52.8 mmol). The mixture was stirred for 2 hours at room temperature. HPLC analysis showed that the reaction was complete. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The resulting crude product was dissolved in DMSO (4 mL) and purified by HPLC. The product was dried for 2 days under vacuum to give 28 mg of the title compound as a white solid (26% yield). MS: m/z=435.66 [M−16]+. 1H NMR (MeOD, 400 MHz): δ=8.24-8.30 (m, 1H), 8.09-8.14 (m, 1H), 7.92-7.96 (m, 1H), 7.56-7.65 (m, 2H), 4.45-4.57 (m, 2H), 2.65-2.69 (m, 2H), 2.26-2.46 (m, 4H), 2.18-2.26 (m, 2H), 1.87-1.97 (m, 2H), 1.45-1.58 (m, 2H), 1.18-1.31 (m, 2H), 1.06-1.17 (m, 1H), 0.92 (s, 9H)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. dissolutionThe resulting crude product was dissolved in DMSO (4 mL)
  4. custompurified by HPLC
  5. customThe product was dried for 2 days under vacuum

Sources & evidence

ORD record
ord-9fdb5e9d0c314ad9a0374311b0840dd9
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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