(+)-1-(1-Naphthyl)ethylamine → {3-[(1r,3r/s)-3-((1r)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-5-trifluoromethyl-phenoxy}-acetic acid

HRID 1627072Notes

Reaction equation

HRID 1627072 reaction equation
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:8]=[C:9]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=2)[O:10][CH2:11][C:12]([O:14]CC)=[O:13])[CH2:3]1.[C:24]1([C@H:34]([NH2:36])[CH3:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>>[C:24]1([C@H:34]([NH:36][CH:2]2[CH2:6][CH2:5][C@@H:4]([C:7]3[CH:8]=[C:9]([CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=3)[O:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:3]2)[CH3:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 49834558ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate

Product 1

HCID 67693578{3-[(1r,3r/s)-3-((1r)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-5-trifluoromethyl-phenoxy}-acetic acid

Procedure

General procedure A was followed using ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate as the ketone and (R)-1-naphthalen-1-yl-ethylamine as the amine. The resulting mixture of isomeric esters was purified and separated by flash chromatography (gradient of 0-80% EtOAc in heptane containing 2.5% NEt3). The faster eluting peak was isolated and subjected to hydrolysis following general procedure B to afford the title compound. 1H NMR (300 MHz, DMSO) δ 8.26 (d, J=8.0 Hz, 1H), 7.98-7.91 (m, 1H), 7.83 (t, J=7.7 Hz, 2H), 7.60-7.47 (m, 3H), 7.10-7.03 (m, 2H), 6.94 (s, 1H), 4.90 (q, 1H), 4.51 (s, 2H), 3.21-3.07 (m, 1H), 3.00-2.83 (m, 1H), 2.29-2.15 (m, 1H), 1.93-1.51 (m, 5H), 1.49 (d, J=6.5 Hz, 3H).

Workup

  1. customwas purified
  2. customseparated by flash chromatography (gradient of 0-80% EtOAc in heptane containing 2.5% NEt3)
  3. washThe faster eluting peak
  4. customwas isolated
  5. customsubjected to hydrolysis

Sources & evidence

ORD record
ord-1136e74deec34b0db7c5c4940da41531
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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