Water → HCID 70359897, compound

HRID 1651678Notes

Reaction equation

HRID 1651678 reaction equation
[NH2:1][CH2:2][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.[CH2:20]([N:27]=[C:28]=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>N1C=CC=CC=1>[CH2:20]([NH:27][C:28](=[O:29])[NH:1][CH2:2][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)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 76639Benzyl isocyanateHCID 14621518HCID 14621518, compound

Product 1

HCID 70359897HCID 70359897, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R,4R,5S)-4-aminomethyl-5-[(Z) -6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (13 mg) in pyridine (0.3 ml) was added benzyl isocyanate (0.02 ml) and the mixture was stirred at room temperature for 60 minutes. Water (0.1 ml) was added and the solvent was evaporated in vacuo to give (2R,4R,5S)-4-(3-benzylureidomethyl)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane as a residue. The residue was dissolved in methanol (1.5 ml) and added 0.3 ml of 1N aqueous sodium hydroxide 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 ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated to dryness and the crude product was purified with preparative TLC (ethyl acetate as an eluent) to give (2R,4R,5S)-4-(3 -benzylureidomethyl)-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-1,3-dioxane (20 mg).

Workup

  1. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0c32ecb076e8420897c84e4b938b8142
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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