Water → HCID 11101768, compound

HRID 1584354Notes

Reaction equation

HRID 1584354 reaction equation
C([O:4][C@H:5]([CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)[O:26][C:27]=2[CH3:28])=[C:17]([O:34][CH3:35])[CH:16]=1)[C:6]([O:8][CH:9](C)C)=[O:7])(=O)C.O>Cl>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:25]1[O:26][C:27]([CH3:28])=[C:23]([CH2:22][O:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][C@@H:5]([OH:4])[C:6]([O:8][CH3:9])=[O:7])=[CH:16][C:17]=2[O:34][CH3:35])[N:24]=1

Participants

4

Reactant 2

HCID 962WaterHCID 10929006HCID 10929006, compound

Product 1

HCID 11101768HCID 11101768, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Isopropyl (R)-(+)-2-acetoxy-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]pentanoate (4.87 g) was dissolved in methanolic HCl (5%, 100 ml), which was stirred for 12 hours at room temperature. The solution was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:1), was obtained methyl (R)-(-)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxypentanoate (3.2 g, 77%), which was recrystallized from ethyl acetate-isopropyl ether to give colorless prisms, m.p.83-84° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washFrom the fraction eluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-781da22656eb4f689bb0013a198a5b7b
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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