Water → HCID 10916695, compound

HRID 1584355Notes

Reaction equation

HRID 1584355 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:32])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C@H:22]([OH:29])[C:23]([O:25][CH:26](C)C)=[O:24])=[CH:15][C:14]=2[O:30][CH3:31])[N:10]=1.O>Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:32])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C@H:22]([OH:29])[C:23]([O:25][CH3:26])=[O:24])=[CH:15][C:14]=2[O:30][CH3:31])[N:10]=1

Participants

4

Reactant 2

HCID 962WaterHCID 11144722HCID 11144722, compound

Product 1

HCID 10916695HCID 10916695, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Isopropyl (S)-(-)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxypentanoate (3.55 g) was dissolved in methanolic HCl (5%, 100 ml). The solution was stirred for 10 hours at room temperature, which was poured into water, followed by 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 (S)-(+)-5-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]-2-hydroxypentanoate (3.03 g, 91%). Recrystallization from ethyl acetate-hexane gave colorless prisms, m.p.80-81° C. [α]D +3.03° (c=1. 0, CHCl3)

Workup

  1. extractionfollowed by 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-8a694e029e5443038698b5401b3a96b1
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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