Water → HCID 70184273, compound

HRID 863339Notes

Reaction equation

HRID 863339 reaction equation
[CH3:1][Si:2]([CH3:32])([CH3:31])[O:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH3:30])[CH:15]=[CH:16][CH:17]([C@@:19]1([CH3:29])[O:23][C@H:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[O:21][C:20]1=[O:28])[OH:18].Cl[C:34]([O:36][CH3:37])=[O:35].C(OCC)(=O)C.O>CN(C)C1C=CN=CC=1.ClCCl>[CH3:32][Si:2]([CH3:1])([CH3:31])[O:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH3:30])[CH:15]=[CH:16][CH:17]([C@@:19]1([CH3:29])[O:23][C@H:22]([C:24]([CH3:26])([CH3:25])[CH3:27])[O:21][C:20]1=[O:28])[O:18][C:34]([O:36][CH3:37])=[O:35]

Participants

7

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8857Ethyl Acetate2×HCID 57140232HCID 57140232, compound

Product 1

HCID 70184273HCID 70184273, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 1.24 g amount of (5R,2S)-5-{(4R)-4-[(1R, 7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-y l]-1-hydroxy-2-penten-1-yl}-5-methyl-2-t-butyl-1, 3-dioxolan-4-one and 1.0 g of 4-dimethylaminopyridine were dissolved in 15 ml of dichloromethane in a 50 ml eggplant-shaped flask. The solution was stirred under ice-cooling while slowly adding 315 μl of methyl chloroformate, then was stirred at the same temperature for 15 minutes and at room temperature for 1.5 hours. A 100 ml amount of ethyl acetate and 30 ml of water were added for separation, and extraction was performed from the aqueous layer by 50 ml of ethyl acetate. The organic layer was washed by a saturated aqueous solution of potassium hydrogensulfate, a saturated aqueous solution of sodium hydrogencarbonate, and saturated saline and was dried over anhydrous magnesium sulfate. The desiccant was filtered out, then the filtrate was concentrated under reduced pressure to obtain a crude product in an amount of 3.61 g. This was purified by a silica column (hexane/ethyl acetate=19/1 to 9/1) to obtain (5R,2S)-5-{(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-1-methoxycarbonyloxy-2-penten-1-yl}-5-methyl-2-t-butyl-1,3-dioxolan-4-one in an amount of 1.388 g (98%).

Workup

  1. temperaturecooling while
  2. stirringwas stirred at the same temperature for 15 minutes and at room temperature for 1.5 hours
  3. washThe organic layer was washed by a saturated aqueous solution of potassium hydrogensulfate
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and saturated saline and was dried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered out
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto obtain a crude product in an amount of 3.61 g
  8. customThis was purified by a silica column (hexane/ethyl acetate=19/1 to 9/1)

Sources & evidence

ORD record
ord-0d4de7d6c2cc4895864255877415ebc4
Source dataset
uspto-grants-1998_02
Patent number
US05719297

Reaction notes

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