Lactic Acid → HCID 86740463, compound

HRID 653288Notes

Reaction equation

HRID 653288 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10][OH:11])[C@H:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:22].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(O)(=O)C(C)O>N1C=CC=CC=1.C(OCC)(=O)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10][O:11][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:39])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[C@H:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]1=[O:22]

Participants

7

Reactant 3

HCID 612Lactic AcidHCID 73974-Toluenesulfonyl chlorideHCID 70390815HCID 70390815, compound

Product 1

HCID 86740463HCID 86740463, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under stirring at 0° C., 1.73 g of cis-1-(2,4-dimethoxybenzyl)-4-hydroxymethyl-3-phenylacetamido-2-oxoazetidine is added to a solution of 1.12 g of p-toluenesulfonyl chloride in 6 ml of pyridine. The reaction mixture is stirred for 2 hours and then allowed to stand overnight in a refrigerator. To the reaction mixture is added 0.68 ml of lactic acid and the mixture is stirred for one hour. The reaction mixture is diluted with 45 ml of ethyl acetate and 15 ml of tetrahydrofuran, and then washed with dilute hydrochloric acid, and aqueous sodium chloride solution, an aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution in this order. The organic solution is dried over magnesium sulfate and the solvent is distilled off in vacuo. To the residue is added a mixed solvent of ether and ethyl acetate (5:1) and the resulting crystals are collected by filtration to give 2.21 g (91%) of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-4-(p-toluenesulfonyloxymethyl)-2-oxoazetidine, m.p. 109°-110° C.

Workup

  1. stirringThe reaction mixture is stirred for 2 hours
  2. stirringthe mixture is stirred for one hour
  3. washwashed with dilute hydrochloric acid, and aqueous sodium chloride solution
  4. dry with materialThe organic solution is dried over magnesium sulfate
  5. distillationthe solvent is distilled off in vacuo
  6. additionTo the residue is added a mixed solvent of ether and ethyl acetate (5:1)
  7. filtrationthe resulting crystals are collected by filtration

Sources & evidence

ORD record
ord-f11c29c1daa745069eecdbdbc3f0b7c9
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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