Reaction #710534

ord-c86ac210310144618949b44cd09a606b

Reaction equation

CS(=O)(=O)O
Methanesulfonic acid
CC(C)(C)OC(=O)N[C@H](C(=O)O)C(C)(C)C
(S)—N-(tert-butoxycarbonyl)-tert-leucine
CCN(CC)CC
triethylamine
CC(C)(C)[C@H](N)C(=O)O
titled compound
CC(C)(C)[C@H](N)C(=O)O
(S)-tert-leucine

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Othera solid was precipitated
  2. 2
    OtherThe solid was sufficiently precipitated
  3. 3
    workup.STIRRINGthe solution was stirred at 25° C. for 30 minutes
  4. 4
    workup.STIRRINGfurther stirred at 25° C. for 30 minutes
  5. 5
    OtherThereafter, the solid was separated by filtration under reduced pressure
  6. 6
    WashThe solid was washed with methylene chloride (5 mL)
  7. 7
    Otherdrying

Procedure

Methanesulfonic acid (576 mg, 6 mmol) was added to a solution of (S)—N-(tert-butoxycarbonyl)-tert-leucine (1155 mg, 5 mmol) and methylene chloride (5 mL), and the mixture was stirred at 25° C. for 3 hours. When triethylamine (708 mg, 7 mmol) was added thereto, a solid was precipitated. The solid was sufficiently precipitated, and then the solution was stirred at 25° C. for 30 minutes and further stirred at 25° C. for 30 minutes. Thereafter, the solid was separated by filtration under reduced pressure. The solid was washed with methylene chloride (5 mL), and then was subjected to vacuum drying. Thereby, the titled compound was produced as a white solid (514 mg, yield of 75%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09302980B2uspto-grants-2016_04