Water → HCID 14621512, compound

HRID 1651675Notes

Reaction equation

HRID 1651675 reaction equation
[OH: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:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>N1C=CC=CC=1>[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[CH2:2][O:1][C:27](=[O:28])[NH:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 14621469HCID 14621469, compound

Product 1

HCID 14621512HCID 14621512, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2R,4R,5S)-4-hydroxymethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (108 mg) in pyridine (0.5 ml) was added phenyl isocyanate (0.1 ml) and the mixture was stirred at room temperature for 30 minutes. Water (1 ml) was added and extracted with ether and the organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the crude product was purified with preparative TLC (hexane:ether=1:1) to give (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-phenylcarbamoyloxymethyl-1,3-dioxane (140 mg).

Workup

  1. extractionextracted with ether
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe crude product was purified with preparative TLC (hexane:ether=1:1)

Sources & evidence

ORD record
ord-3e743e72c382455b88aee602bd9d513a
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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