2-Methyl-2,3-methylene-6-(1-cyclopropylethoxy)carbonylaminopenam-3-carboxylic acid → 2-Methyl-2,3-methylene-6-aminopenam-3-carboxylic acid

HRID 1287321Notes

Reaction equation

HRID 1287321 reaction equation
[CH3:1][C:2]12[CH2:10][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:11](=[O:22])[CH:12]([NH:13]C(OC(C3CC3)C)=O)[C@H:4]1[S:3]2>C(O)=O>[CH3:1][C:2]12[CH2:10][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:11](=[O:22])[CH:12]([NH2:13])[C@H:4]1[S:3]2

Participants

3

Reactant 1

HCID 681322652-Methyl-2,3-methylene-6-(1-cyclopropylethoxy)carbonylaminopenam-3-carboxylic acid

Product 1

HCID 681320312-Methyl-2,3-methylene-6-aminopenam-3-carboxylic acidYield 68.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

A solution of 2-methyl-2,3-methylene-6-(1-cyclopropylethoxy)carbonylaminopenam-3-carboxylic acid(840 mg.) in formic acid(5 ml.) was stirred for 1.5 hours at room temperature. After the reaction, formic acid was distilled off under reduced pressure. The residue was washed with ether, crystallized by adding acetonitrile containing water and the crystals were collected by filtration to give 2-methyl-2,3-methylene-6-aminopenam-3-carboxylic acid(380 mg.), mp. 200°C (dec.).

Workup

  1. distillationwas distilled off under reduced pressure
  2. washThe residue was washed with ether
  3. customcrystallized
  4. additionby adding acetonitrile
  5. additioncontaining water
  6. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-6675a06ce1f541ceb18952874c8c5c62
Source dataset
uspto-grants-1976_10
Patent number
US03984397

Reaction notes

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