Water → HCID 14621536, compound

HRID 1651683Notes

Reaction equation

HRID 1651683 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]([OH:17])=[O:16])[CH2:7][O:6][C@@H:5]([CH3:18])[O:4]1.[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>N1C=CC=CC=1.C(OCC)(=O)C>[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]([CH3:18])[O:4][C@H:3]1[CH2:2][NH:1][C:26]([NH:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27])([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 14621534HCID 14621534, compound

Product 1

HCID 14621536HCID 14621536, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R,5S)-4-aminomethyl-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-1,3-dioxane (50 mg) in pyridine (0.5 ml) was added phenylisocyanate (0.1 ml) and stirred at room temperature for 1 hour. To this mixture water (1 ml) was added and stirred for 2 hours. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with 1N hydrochloric acid. The organic layer was evaporated in vacuo and the crude residue was purified with preparative TLC to give (2R,4R,5S)-5-[(Z)-6-carboxy-2-hexenyl]-2-methyl-4-(3-phenylureidomethyl)-1,3-dioxane (27 mg).

Workup

  1. stirringstirred for 2 hours
  2. washthe organic layer was washed with 1N hydrochloric acid
  3. customThe organic layer was evaporated in vacuo
  4. customthe crude residue was purified with preparative TLC

Sources & evidence

ORD record
ord-63cada9bf4ae485e9a868a65595f8408
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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