Water → HCID 15233245, compound

HRID 1608706Notes

Reaction equation

HRID 1608706 reaction equation
CC1(C)CO[C:5]2([CH:7]=[C:6]2[CH:8]([OH:22])[C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:11][CH2:12][CH3:13])[O:4]C1.S(=O)(=O)(O)O.O>C(OCC)C.O1CCCC1>[C:18]([O:17][C:15]([NH:14][C@@H:9]([CH2:10][CH2:11][CH2:12][CH3:13])[CH:8]([C:6]1[C:5](=[O:4])[CH:7]=1)[OH:22])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 15233228HCID 15233228, compound

Product 1

HCID 15233245HCID 15233245, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.80 g of 2-((2S)-2-tert-Butoxycarbonylamino-1-hydroxyhexyl) cyclopropenone 2,2-dimethyl-1.3-propanediyl acetal obtained in Example 5 in 100 ml of diethyl ether and 20 ml of tetrahydrofuran were added 0.2 ml of 2 N sulfuric acid and 1 ml of water, and the mixture was stirred for 30 minutes. After subsequent addition of 300 ml of ether, the resulting product was washed sequentially in 50 ml of an aqueous 0.01 N sodium hydroxide solution and an aqueous saturated brine. After drying over magnesium sulfate, the product was filtered and concentrated, followed by purification by silica gel column chromatography (eluent; hexane: ethyl acetate =1:2) to produce the objective product (3.15 g).

Workup

  1. washthe resulting product was washed sequentially in 50 ml of an aqueous 0.01 N sodium hydroxide solution
  2. dry with materialAfter drying over magnesium sulfate
  3. filtrationthe product was filtered
  4. concentrationconcentrated
  5. customfollowed by purification by silica gel column chromatography (eluent; hexane: ethyl acetate =1:2)

Sources & evidence

ORD record
ord-e3d6fe8f43df42b5b050a3a8c50ad511
Source dataset
uspto-grants-1995_03
Patent number
US05395958

Reaction notes

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