Acetic Acid → HCID 131716592, compound

HRID 1088034Notes

Reaction equation

HRID 1088034 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>O1CCCC1>[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.[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

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131716592HCID 131716592, compound

Product 2

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This product (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 for two nights as in Example B'-12 to give 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) and 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).

Workup

  1. customkept at room temperature for two nights as in Example B'-12

Sources & evidence

ORD record
ord-17d374e50a164247a5aaeb1d2406ce93
Source dataset
uspto-grants-1990_10
Patent number
US04960879

Reaction notes

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