Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68691509, compound

HRID 2266255Notes

Reaction equation

HRID 2266255 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C@:8]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)([C:10]1[CH:11]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)[C:13]([F:16])=[CH:14][CH:15]=1)O)(=[O:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1(C)C=CC=CC=1>[C:1]([NH:4][CH2:5][CH2:6][CH:7]=[C:8]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)[C:10]1[CH:11]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=2)[C:13]([F:16])=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 57918883HCID 57918883, compound

Product 1

HCID 68691509HCID 68691509, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (R)-tert-butyl 3-((S)-4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)-1-hydroxybutyl)piperidine-1-carboxylate (380 mg, 0.76 mmol) in anhydrous toluene (8 mL) was added Burgess reagent (352 mg, 1.47 mmol). The reaction mixture was stirred under reflux overnight. The solvent was removed and the residue was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residual oil was purified by preparative tlc to afford (S)-tert-butyl 3-(4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)but-1-enyl)piperidine-1-carboxylate (110 mg, 30% yield). 1H NMR (400 MHz, MeOH):7.33-7.39 (m, 2 H), 7.13-7.23 (m, 2 H), 6.95-7.03 (m, 3 H), 5.29-5.33 (m, 1 H), 3.93-4.15 (m, 1 H), 3.78-3.91 (m, 1 H), 3.00-3.04 (m, 2H), 2.40-2.53 (m, 1 H), 2.37 (d, 3 H), 1.89 (s, 3 H), 1.75 (m, 1H), 1.44-1.62 (m, 4 H), 1.41 (s, 9 H), 1.16-1.32 (m, 3H), 1.01 (m, 1 H). MS (E/Z): 481 (M+H+)

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent was removed
  3. customthe residue was partitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residual oil was purified by preparative tlc

Sources & evidence

ORD record
ord-69a9ef2b49bf40e6b9f9aee9484ecfa9
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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