Triethylamine → HCID 66858871, compound

HRID 2179760Notes

Reaction equation

HRID 2179760 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][C@@H:14]([C:16]([OH:18])=O)[C:13]1([CH3:20])[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]1[CH:22]=[CH:23][C:24]2N(O)N=[N:27][C:25]=2C=1.C(C1CCN([C:39]([O-:41])=[O:40])CC1)C.[CH3:42][CH2:43]N(CC)CC>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][C@@H:14]([C:16]([N:27]2[CH2:21][CH2:22][CH:23]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:24][CH2:25]2)=[O:18])[C:13]1([CH3:20])[CH3:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 58111002HCID 58111002, compoundHCID 86650120HCID 86650120, compound

Product 1

HCID 66858871HCID 66858871, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1R,3S)-3-(benzyloxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (1.5 g, 5.415 mmol) in DCM (20 ml) EDCI (1.55 g, 8.122 mmol) and HOBt (1.24 g, 8.122 mmol) were added at 0° C. after 10 minutes, 4-ethylpiperidinecarboxylate (1.0 g, 6.498 mmol) and Et3N (3.75 ml, 27.075 mmol) were added drop wise and the reaction mass was allowed to stir at room temperature for 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with DCM and washed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine and the organic layer was concentrated under reduced pressure, the resulting crude residue was stirred in hexane, and the obtained solid was filtered and dried under vacuum. Wt: 1.3 g; Yield: 57.7%. 1H NMR (300 MHz, CDCl3): δ 7.35 (5H, s), 5.194-5.058 (3H, m), 4.506-4.3 (1H, m), 4.19-4.11 (2H, m), 3.98-3.78 (2H, m), 3.15-3.00 (1H, m), 2.9-2.7 (2H, m), 2.6-2.2 (3H, m), 2.0-1.8 (2H, m), 1.741.5 (2H, m), 1.26 (3H, s), 1.2 (3H, m), 0.85 (3H, s); Mass: [M+1]+ 417 (10%), [M+Na]+ 439 (100%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. washwashed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. stirringthe resulting crude residue was stirred in hexane
  5. filtrationthe obtained solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6d819f5b87b54c99b13ef06499230db8
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…