Acetone → HCID 70257737, compound

HRID 1952838Notes

Reaction equation

HRID 1952838 reaction equation
C(O[CH2:5][C@H:6]1[C@H:10]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:8][C:7]1=[O:16])(=O)C.C([NH:20][C@H:21]([C:24]([OH:26])=[O:25])[CH2:22][SH:23])(=O)C.[OH-].[Na+].CO.[CH3:31][C:32](C)=[O:33]>>[C:13]([O:12][CH2:11][C@@H:10]1[CH2:9][CH2:8][C:7](=[O:16])[C@H:6]1[CH2:5][S:23][CH2:22][C:21]([NH2:20])([C:32](=[O:33])[CH3:31])[C:24]([OH:26])=[O:25])(=[O:15])[CH3:14]

Participants

6

Reactant 5

HCID 180AcetoneHCID 887MethanolHCID 12035N-Acetyl-L-CysteineHCID 14798Sodium HydroxideHCID 53699935HCID 53699935, compound2×

Product 1

HCID 70257737HCID 70257737, compoundYield 86.9%

Procedure

A solution of trans-2,3-bis(acetoxymethyl)-cyclopentanone [Compound (a)] (205 mg, 0.899 mmol) in acetone (7.2 ml) was added to N-acetyl-L-cysteine (147 mg, 0.899 mmol), and then added IN-sodium hydroxide (1.8 ml), stirred at room temperature for 15 minutes. The reaction solution was concentrated. The residue was purified by Sephadex LH-20 (11.80% aqueous methanol) to obtain the compound (II) (276 mg, yield 86.9%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customThe residue was purified by Sephadex

Sources & evidence

ORD record
ord-db80869baca2411d92e9fa6c41a38739
Source dataset
uspto-grants-2000_09
Patent number
US06114364

Reaction notes

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