Acetic Acid → HCID 131716592, compound

HRID 1088030Notes

Reaction equation

HRID 1088030 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:15]3[C:16](=[O:21])[C@H:17]([CH:18]([OH:20])[CH3:19])[C@H:14]3[CH:13]([CH2:22][CH3:23])[C:12]=2[CH2:24][S:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[O:10])=[CH:5][CH:4]=1.C(O)(=O)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[N:15]3[C:16](=[O:21])[C@H:17]([CH:18]([OH:20])[CH3:19])[C@H:14]3[CH:13]([CH2:22][CH3:23])[C:12]=2[CH2:24][S:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[O:10])=[CH:32][CH:33]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([CH:11]2[N:15]3[C:16](=[O:21])[C@H:17]([CH:18]([OH:20])[CH3:19])[C@H:14]3[CH:13]([CH3:22])[C:12]2=[CH:24][S:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[O:10])=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86584982Sodium bicarbonate ethyl acetateHCID 131716592HCID 131716592, compound

Product 2

HCID 70398597HCID 70398597, compoundYield 6%HCID 131716592HCID 131716592, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This silylate (b) (2.1 g; 3.69 millimoles) is dissolved in tetrahydrofuran (10 ml), mixed with acetic acid (0.8 ml) and tetrabutylammonium fluoride trihydrate (2.78 g; 2.4 equivalents) and kept at room temperature two nights. The reaction mixture is poured into aqueous sodium hydrogen carbonate-ethyl acetate. The organic layer is separated, washed with water, dried, and concentrated in vacuum, and purified by chromatography (Lober B, ethyl acetate) to give 6α-(1-hydroxyethyl)-1-methyl-2-(4-pyridylthio)methyl-1-carbapen-2-em-3-carboxylic acid p-methoxybenzyl ester (b) (455 mg; Yield: 27.1%; having physical constants as follows from polar fraction) and 6α-(1-hydroxyethyl)-1-methyl-2-(4-pyridylthio)methylidene-1-carbapenam-3-carboxylic acid p-methoxybenzyl ester (100 mg; Yield: 6.0%, from less polar fraction). IR (CHCl3)ν: 3400-3120br, 1750br, 1604, 1575 cm-1.

Workup

  1. waitkept at room temperature two nights
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuum
  6. custompurified by chromatography (Lober B, ethyl acetate)

Sources & evidence

ORD record
ord-7310ac9a0f3542c5aa227926a9ac9697
Source dataset
uspto-grants-1990_10
Patent number
US04960879

Reaction notes

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