Thiophene-2-carbohydrazide → HCID 70359991, compound

HRID 1651679Notes

Reaction equation

HRID 1651679 reaction equation
[CH:1]([C@H:3]1[C@@H:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][O:6][C@@H:5]([CH3:19])[O:4]1)=O.[C:20]1([C:25]([NH:27][NH2:28])=[O:26])[S:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][C@H:8]1[CH2:7][O:6][C@@H:5]([CH3:19])[O:4][C@H:3]1[CH2:1][NH:28][NH:27][C:25](=[O:26])[C:20]1[S:24][CH:23]=[CH:22][CH:21]=1)=[O:16]

Participants

7

Reactant 4

HCID 73098Thiophene-2-carbohydrazideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 14621471HCID 14621471, compound

Product 1

HCID 70359991HCID 70359991, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of (2R,4R,5S)-4-formyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (47 mg) in ethanol (1 ml) was added thenohydrazide (27 mg) and the mixture was stirred at room temperature for 1 hour, and then added sodium cyanoborohydride (20 mg) and acetic acid (0.25 ml) and the mixture was stirred for 1 hour. Aqueous sodium bicarbonate was added and extracted with chloroform and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to give (2R,4R,5S) -5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-(N'-thenoylhydrazino)methyl-1,3-dioxane as a residue and the residue was dissolved in methanol (2 ml) and added 1N aqueous sodium hydroxide (0.4 ml) and stirred at room temperature for 4 hours. The reaction mixture was evaporated in vacuo and the residue was neutralized with 1N hydrochloric acid and extracted with chloroform. The organic layers were combined and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product was purified with preparative TLC (ethyl acetate as an eluent) to give (2R,4R,5S)-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-4-(N'-thenoylhydrazino)methyl-1,3-dioxane (55 mg).

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5b9024b469ef48389e3c745e4b7419b6
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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