HCID 131719459, compound → HCID 131719458, compound

HRID 1489844Notes

Reaction equation

HRID 1489844 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][S:9][C:8]([N:11]2[CH2:14][CH:13]([S:15][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([O:23]CC3C=CC([N+]([O-])=O)=CC=3)=[O:22])[CH2:12]2)=[N:7]1>O1CCCC1.P([O-])([O-])([O-])=O.[Zn]>[CH3:1][O:2][CH2:3][O:4][CH2:5][C@@H:6]1[CH2:10][S:9][C:8]([N:11]2[CH2:12][CH:13]([S:15][C:16]3[C@H:17]([CH3:40])[C@@H:18]4[C@@H:35]([C@H:36]([OH:38])[CH3:37])[C:34](=[O:39])[N:19]4[C:20]=3[C:21]([OH:23])=[O:22])[CH2:14]2)=[N:7]1

Participants

5

Reactant 1

HCID 131719459HCID 131719459, compound

Product 1

HCID 131719458HCID 131719458, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 756 mg of Compound (30) obtained in Example 3 in 10 ml of tetrahydrofuran and 30 ml of 0.35 M phosphate buffer (pH 6.0) solution was added 6.0 g of zinc powder, and the reaction mixture was stirred for 2 hours at room temperature. After removal of the zinc powder by filtration, the filtrate was washed with ethyl acetate and the pH of the filtrate was adjusted to 5.5, then the filtrate was concentrated. The resulting residue was purified by using Diaion HP-40R column (10% isopropanol-water) to give 415 mg (71%) of (1R,5S,6S)-2-[1-((4R)-methoxymethyloxymethyl-1,3-thiazolin-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylic acid [Compound (31)].

Workup

  1. customAfter removal of the zinc powder
  2. filtrationby filtration
  3. washthe filtrate was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-3f6cb39bf1f74c16830b104bace81913
Source dataset
uspto-grants-1997_10
Patent number
US05679790

Reaction notes

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