Methanol → HCID 54203677, compound

HRID 1742206Notes

Reaction equation

HRID 1742206 reaction equation
Cl.C[O:3][C:4](=[O:14])[C@H:5]([CH3:13])[NH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:15](=[O:26])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CO>C1(C)C=CC=CC=1.C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:15]([N:6]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[C@H:5]([C:4]([OH:3])=[O:14])[CH3:13])=[O:26])[CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 887MethanolHCID 531671-MethylpiperazineHCID 94429TriphosgeneHCID 20613011HCID 20613011, compound

Product 1

HCID 54203677HCID 54203677, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To Cyclohexylalanine methyl ester hydrochloride salt (1.00 g, 4.51 mmol) suspended in toluene (25 mL) was added bis (trichloromethyl) carbonate (triphosgene) (669.2 mg, 0.5 equiv). The reaction mixture was warmed at 100° C. for 3 hours and then concentrated under reduced pressure to afford a semi-solid residue. To this residue dissolved in methylene chloride (15 mL) and cooled to 0° C. was added N-methylpiperazine (0.50 mL, 1.0 equiv). After stirring for 1 hour, the reaction mixture was concentrated at reduced pressure to afford a semi-solid residue. Flash chromatography on silica gel eluting with 4% methanol in chloroform afforded the title product (629 mg, 45%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford a semi-solid residue
  3. temperaturecooled to 0° C.
  4. concentrationthe reaction mixture was concentrated at reduced pressure
  5. customto afford a semi-solid residue

Sources & evidence

ORD record
ord-87a79a52157c4333b06626b6c2ad47df
Source dataset
uspto-grants-1994_08
Patent number
US05338726

Reaction notes

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