Pyridine → HCID 178450889, compound

HRID 1497522Notes

Reaction equation

HRID 1497522 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[NH:10][C:11]1[CH:31]=[CH:30][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](O)=[O:27])=[C:20]([Cl:29])[CH:19]=2)=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(N(C)C)=C(C)C.[C:48]([O:52][C:53](=[O:70])[CH2:54][C:55]1[CH:56]=[C:57]([NH:61][CH2:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH:58]=[CH:59][CH:60]=1)([CH3:51])([CH3:50])[CH3:49].N1C=CC=CC=1>ClCCl.O>[C:36]([O:35][C:33]([NH:32][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([N:61]([CH2:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C:57]3[CH:58]=[CH:59][CH:60]=[C:55]([CH2:54][C:53]([O:52][C:48]([CH3:50])([CH3:51])[CH3:49])=[O:70])[CH:56]=3)=[O:27])=[C:20]([Cl:29])[CH:19]=2)=[O:16])=[CH:30][CH:31]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 90281955HCID 90281955, compoundHCID 178454289HCID 178454289, compound

Product 1

HCID 178450889HCID 178450889, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[4-({4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoyl}oxy)-2-chlorophenyl]propanoic acid (200 mg) in dichloromethane (3.00 mL) was added 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.0700 mL) under ice-cooling, followed by stirring at room temperature for 1 hour. Under ice-cooling, a solution of tert-butyl N-[3-(2-tert-butoxy-2-oxoethyl)phenyl]glycinate (170 mg) and pyridine (0.0500 mL) in dichloromethane (3.00 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4-(3-{(2-tert-butoxy-2-oxoethyl)[3-(2-tert-butoxy-2-oxoethyl)phenyl]amino}-3-oxopropyl)-3-chlorophenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (210 mg).

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. stirringby stirring at room temperature overnight
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-261017e8d55e4e91a6e36186e307b484
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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