Hydrochloric Acid → Boc-leu-chloromethylketone

HRID 1380606Notes

Reaction equation

HRID 1380606 reaction equation
[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:7]([CH:9]=[N+]=[N-])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[ClH:19]>CCOCC>[NH:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:2]([C:7]([CH2:9][Cl:19])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54542344(3S)-3-[(tert-Butoxycarbonyl)amino]-1-diazonio-5-methylhex-1-en-2-olate

Product 1

HCID 7020822Boc-leu-chloromethylketone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Boc-LeuCHN2 (4.40 g, 17.2 mmoles) was dissolved in 50 mL of ether and cooled to 0°; anhydrous 3.45N ethanolic:HCl (5.22 mL, 18.0 mmoles) was added. After about 5 minutes, the resulting solution was washed with cold water, saturated aqueous sodium chloride, and was dried over anhydrous sodium sulfate. Solvent was evaporated to yield crystalline Boc-LeuCH2Cl. Product was isolated and washed with petroleum ether to yield 0.84 g (mp 65°-66°) in a first crop and 1.94 g (mp 64°-65.5°) in a second crop isolated from cold petroleum ether.

Workup

  1. temperaturecooled to 0°
  2. washthe resulting solution was washed with cold water, saturated aqueous sodium chloride
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customSolvent was evaporated

Sources & evidence

ORD record
ord-fb012de6e5dd49b0a50e317f031fd54a
Source dataset
uspto-grants-1986_04
Patent number
US04582821

Reaction notes

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