Triethylamine → HCID 68421687, compound

HRID 2061253Notes

Reaction equation

HRID 2061253 reaction equation
Cl.[CH:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:7](=[C:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:26])[CH2:24][NH2:25])[CH2:19][CH2:18]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@@H:35]1[C:39](O)=[O:40])=[O:33])([CH3:30])([CH3:29])[CH3:28].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[CH:13]1[C:9]2[CH:10]=[CH:11][C:12]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[C:7](=[C:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:26])[CH2:24][NH:25][C:39]([CH:35]4[CH2:36][CH2:37][CH2:38][N:34]4[C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])=[O:40])[CH2:21][CH2:22]3)[C:8]=2[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68420335HCID 68420335, compound

Product 1

HCID 68421687HCID 68421687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

700 mg (1.91 mmol) of the compound of Example 2, 493 mg (2.29 mmol) of (R)-1-(t-butoxycarbonyl)-2-pyrrolidinecarboxylic acid and 512 mg (2.67 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride were dissolved in 20 ml of dichloromethane. 0.77 ml (5.59 mmol) of triethylamine and 24 mg (0.2 mmol) of dimethylaminopyridine were added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. The solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and they were washed with water. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane:ethyl acetate=9:1 to 1:4) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customThe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the residue, and they
  4. washwere washed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by the silica gel chromatography (hexane:ethyl acetate=9:1 to 1:4)

Sources & evidence

ORD record
ord-f867663d9009404a9e19deaed464e1ef
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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