HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → HCID 57305915, compound

HRID 1075640
Notes
Print preview

Reaction equation

HRID 1075640 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:30][C@H:31]1[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[NH:33][C:32]1=[O:39]>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH:30][C@H:31]1[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[NH:33][C:32]1=[O:39])=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 736104N-carbobenzyloxyalanineHCID 15428308HCID 15428308, compound

Product 1

HCID 57305915HCID 57305915, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-2.5 °C

Procedure

To a solution of N-benzyloxycarbonyl-L-alanine (1.604 g, 7.188 mmole) and triethylamine (799 mg, 7.91 mmole) in dichloromethane (30 ml), ethyl chloroformate (738 mg, 6.83 mmole) was added at -15° C. The reaction mixture was stirred at -10 to 5° C. for 1.5 hrs. Then a precooled (ca. -15° C.) solution of (3S,4S)-3-amino-4-acetoxy-azetidin-2-one in ethyl acetate (see above) was added at -15° C. and the resulting mixture was stirred at 0° C. to room temperature for 2 hrs. After removal of solvent, the residue was dissolved in ethyl acetate, washed with cold saturated NaHCO3 solution, water, brine and dried over sodium sulfate. After removal of solvent, the residue was recrystallized from dichloromethane and (3S,4S)-3-(N-benzyloxycarbonyl-L-alanyl) amino-4-acetoxy-azetidin-2-one was obtained (1.36 g, 54% yield).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. to room temperature for 2 hrs
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with cold saturated NaHCO3 solution, water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-e24e7640b99e4037af6daf6f2436b3b7
Source dataset
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05905076

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes