Water → (cis)-1-benzoyl-4-tosyloxy-L-proline

HRID 1165971Notes

Reaction equation

HRID 1165971 reaction equation
[C:1]([N:9]1[CH2:17][C@@H:16]([O:18][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:15][C@H:10]1[C:11]([O:13]C)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[OH-].[Li+]>C1COCC1>[C:1]([N:9]1[CH2:17][C@@H:16]([O:18][S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:26])=[CH:27][CH:28]=2)(=[O:20])=[O:21])[CH2:15][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 14750327(cis)-1-Benzoyl-4-tosyloxy-L-proline, methyl ester

Product 1

HCID 53847232(cis)-1-benzoyl-4-tosyloxy-L-proline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (cis)-1-benzoyl-4-tosyloxy-L-proline, methyl ester (from the previous step) in THF.H2O (25 ml-5 ml) was stirred under argon and treated with lithium hydroxide mono hydrate (672 mg, 16 mmole). The reaction was stirred for 3 hours, concentrated in vacuo, acidified to pH 1.5 with HCl, and extracted with ethyl acetate. The organic extracts were dried, filtered and concentrated in vacuo to a white solid which was recrystallized twice from ethyl acetate to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid which
  6. customwas recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-a33709a5bc914e348b8470f1ef3ae1ab
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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