Morpholine → HCID 58355495, compound

HRID 1184230Notes

Reaction equation

HRID 1184230 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([N:14]([C:19]([C:21]2[N:22]=[N:23][N:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:25]=2[CH2:26][OH:27])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C@@H:10]([C:34]([OH:36])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.N1(O)C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>C(#N)C.O.C(N(CC)CC)C>[OH:27][CH2:26][C:25]1[N:24]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:23]=[N:22][C:21]=1[C:19]([N:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[C@H:12]1[CH2:11][C@@H:10]([C:34]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[O:36])[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13]1)=[O:20]

Participants

8

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58355124HCID 58355124, compound

Product 1

HCID 58355495HCID 58355495, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

(3R,5S)-1-(tert-Butoxycarbonyl)-5-[{[5-(hydroxymethyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid (2.18 g), 5 morpholine (0.46 ml), 1H-benzotriazol-1-ol (330 mg) and triethylamine (1.5 ml) were dissolved in acetonitrile (20 ml), WSC.HCl (1.25 g) was added and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (2.35 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-5feabec528b0447a9e6dd5fb2c7a4a5f
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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