1-Hydroxybenzotriazole → HCID 68310368, compound

HRID 922419Notes

Reaction equation

HRID 922419 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([NH:14][CH:15]1[CH2:17][CH2:16]1)[CH3:13].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][O:28][C@@H:27]([C:31](O)=[O:32])[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:15]1([N:14]([CH:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)[CH3:13])[C:31]([C@@H:27]2[O:28][CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:26]2)=[O:32])[CH2:17][CH2:16]1

Participants

8

Reactant 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 457921551197803-63-6

Product 1

HCID 68310368HCID 68310368, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[1-(2-naphthyl)ethyl]cyclopropylamine hydrochloride (149 mg), (2R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (208 mg) and 1-hydroxybenzotriazole (122 mg) in N,N-dimethylformamide (6 mL) was added diisopropylethylamine (0.125 μL), and the thereto was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2078 mg) under ice-cooling. The mixture was stirred at room temperature for 19 hours and then to the reaction solution was added 1-normal aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water twice, saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The residue was triturated with n-hexane-diethyl ether (5:1) to give tert-butyl (2R)-2-({cyclopropyl[1-(2-naphthyl)ethyl]amino}carbonyl)morpholine-4-carboxylate [Ex(163-1)] (153 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water twice
  4. dry with materialsaturated saline, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with n-hexane-diethyl ether (5:1)

Sources & evidence

ORD record
ord-da1407435f23426799a968b938b37c90
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

Loading…