Triethylamine → HCID 70804047, compound

HRID 2179759Notes

Reaction equation

HRID 2179759 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:12][C@H:11]([C:13]([OH:15])=O)[C:10]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[CH2:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:29].CCN(CC)CC>C(Cl)Cl>[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:13]([C@H:11]2[CH2:12][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]2([CH3:17])[CH3:16])=[O:15])[CH2:32][CH2:31]1)[CH3:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 791961-EthylpiperazineHCID 15819069HCID 15819069, compound

Product 1

HCID 70804047HCID 70804047, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1S,3R)-3-(tert-butoxycarbonylamino)-2,2-dimethylcyclobutanecarboxylic acid (2 g, 8.23 mmol) in DCM (50 ml) EDCI (946 mg, 9.876 mmol) and HOBt (756 mg, 9.876 mmol) were added at 0° C., after 10 minutes N-Ethyl piperazine (939 mg, 16.46 mmol) and Et3N (3 mL, 41.15 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 obtained solid was filtered. Wt: 1.6 g; Yield: 70%. 1H NMR (300 MHz, CDCl3): δ 4.77 (d, 1H, J=8.4 Hz), 3.89-3.78 (m, 1H), 3.6-3.46 (m, 3H), 2.80 (m, 1H), 2.60-2.40 (m, 8H), 1.80 (m, 1H), 1.43 (s, 9H), 1.12 (s, 3H), 1.2 (t, 3H), 0.87 (s, 3H); Mass: [M+1]+ 340 (25%), [M+Na]+ 362 (100%).

Workup

  1. additionwere added drop wise
  2. customAfter completion of the reaction (monitored by TLC)
  3. washwashed with water, saturated NaHCO3 solution, water, 1N HCl, water and saturated brine
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. stirringThe resulting crude residue was stirred in hexane
  6. customobtained solid
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-47363871c00649898d9c1adbc234ee11
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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