Acetyl chloride → HCID 54557979, compound

HRID 1066290Notes

Reaction equation

HRID 1066290 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:11][OH:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)(=[O:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH3:10])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 54557979HCID 54557979, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(tert-Butoxycarbonyl)-L-alaninol (438 mg, 2.5 mmol) was dissolved in 5 mL of methylene chloride in an ice bath and acetyl chloride (0.294 mL, 3.75 mmol), followed by triethylamine (0.7 mL, 5 mmol) were added. It was then reacted at 0° C. for 1 hour and at room temperature for 2 days. The mixture was diluted with 25 mL of ethyl acetate and the organic layer was washed with 10%-sodium hydrogen carbonate (3x), brine (2x), dried over magnesium sulfate anhydrous, and then evaporated to dryness to yield 380 mg of N-(tert-butoxycarbonyl)-O-acetyl-L-alaninol.

Workup

  1. additionwere added
  2. customIt was then reacted at 0° C. for 1 hour and at room temperature for 2 days
  3. washthe organic layer was washed with 10%-sodium hydrogen carbonate (3x), brine (2x)
  4. dry with materialdried over magnesium sulfate anhydrous
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ae264358f1344d778eb797c8c4d1b6d2
Source dataset
uspto-grants-2001_06
Patent number
US06242494B1

Reaction notes

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