Triethylamine → HCID 69150713, compound

HRID 719388Notes

Reaction equation

HRID 719388 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]1[CH2:13][C@H:12]([CH:14]([CH3:16])[CH3:15])[N:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]1=[O:25].C(N(CC)CC)C.[F:33][C:34]([F:52])([F:51])[C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=2)=[CH:37][CH:36]=1>ClCCl>[CH2:18]([O:17][N:11]1[C@@H:12]([CH:14]([CH3:16])[CH3:15])[CH2:13][C@@H:9]([NH:8][S:47]([C:44]2[CH:43]=[CH:42][C:41]([C:38]3[CH:39]=[CH:40][C:35]([C:34]([F:33])([F:51])[F:52])=[CH:36][CH:37]=3)=[CH:46][CH:45]=2)(=[O:49])=[O:48])[C:10]1=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37201024'-(Trifluoromethyl)[1,1'-biphenyl]-4-sulfonyl chlorideHCID 69151068HCID 69151068, compound

Product 1

HCID 69150713HCID 69150713, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of (3R,5R)-3-amino-1-(Benzyloxy)-5-isopropyl-2-pyrrolidinone trifluoroacetate (0.036 g, 0.10 mmoles), triethylamine (0.070 mL, 0.50 mmoles) and dry dichloromethane (0.70 mL) was added in small portions 4′-(trifluoromethyl)[1,1′-biphenyl]-4-sulfonyl chloride (0.034 g, 0.11 mmoles) during two minutes. The mixture was stirred under dry nitrogen at 22° C. for 60 minutes, concentrated by rotary evaporation, re-dissolved in dichloromethane (2 mL), mixed with a silica (1 g), concentrated again and then applied on a silica column. Elution with ethyl acetate/n-heptane (1:4 through 1:3) and concentration of pure fractions gave 0.030 g (57% yield) of the title compound as a white solid. LC-MS (APCI) m/z 533 (M+1). 1H NMR (CDCl3) δ 8.02 (d, J=8 Hz, 2H), 7.74 (d, J=8 Hz, 2H), 7.72 (d, J=8 Hz, 2H) 7.70 (d, J=8 Hz, 2H), 7.40–7.30 (m, 5H), 5.43 (d, J=3 Hz, 1H), 4.99 (d, J=10 Hz, 1H), 4.88 (d, J=10 Hz, 1H), 3.76 (dt, J1=3 Hz, J2=9 Hz, 1H), 3.31 (ddd, J1=4 Hz, J2=6 Hz, J3=9 Hz, 1H), 2.40 (ddd, J1=7 Hz, J2=9 Hz, J3=13 Hz, 1H), 2.20–2.08 (m, 1H), 1.76 (dt, J1=9 Hz, J2=13 Hz, 1H), 0.85 (d, J=7 Hz, 3H) and 0.83 (d, J=7 Hz, 3H) ppm.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. dissolutionre-dissolved in dichloromethane (2 mL)
  3. additionmixed with a silica (1 g)
  4. concentrationconcentrated again
  5. washElution with ethyl acetate/n-heptane (1:4 through 1:3) and concentration of pure fractions

Sources & evidence

ORD record
ord-7f3af7bdf91548c6a6651397b6aa53a4
Source dataset
uspto-grants-2006_11
Patent number
US07132434B2

Reaction notes

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