Triethylamine → HCID 70096722, compound

HRID 619704Notes

Reaction equation

HRID 619704 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]1[C:20]([OH:22])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:25](CC)CC)C.ClC(OCC)=O.N[C@H:37]1[C@H:40]([O:41][C:42](=[O:44])[CH3:43])[NH:39][C:38]1=[O:45]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]1[C:20]([C@@H:37]1[C@H:40]([O:41][C:42](=[O:44])[CH3:43])[N:39]([NH2:25])[C:38]1=[O:45])=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27764001-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acidHCID 15428308HCID 15428308, compound

Product 1

HCID 70096722HCID 70096722, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-2.5 °C

Procedure

To a solution of 1-benzyloxycarbonyl-2-indoline carboxylic acid (320 mg, 1.05 mmol) and triethylamine (106 mg, 1.05 mmol) in chloroform (20 ml), ethyl chloroformate (109 mg, 1 mmol) was added at -15° C. The reaction mixture was stirred at a bath temperature of -10 to 5° C. for 1 hr. Then a precooled solution of (3S,4S)-3-amino-4-acetoxy-azetidin-2-one in ethyl acetate was added at -15° C. and stirring was continued at a bath temperature of -15 to 5° C. for 1 hr. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:3) as eluent and the title compound was obtained.

Workup

  1. stirringstirring
  2. customwas continued at a bath
  3. waittemperature of -15 to 5° C. for 1 hr
  4. customAfter removal of solvent
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of solvent
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dcb480c362444f43a6970770ca97fa55
Source dataset
uspto-grants-1999_09
Patent number
US05959123

Reaction notes

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