Sodium Hydroxide → 2,4-Thiazolidinedicarboxylic acid, 3-acetyl-2-methyl-

HRID 1503171Notes

Reaction equation

HRID 1503171 reaction equation
CC[O:3][C:4]([C:6]1([CH3:17])[N:10]([C:11](=[O:13])[CH3:12])[CH:9]([C:14]([OH:16])=[O:15])[CH2:8][S:7]1)=[O:5].[OH-].[Na+]>C(O)C>[C:11]([N:10]1[CH:9]([C:14]([OH:16])=[O:15])[CH2:8][S:7][C:6]1([CH3:17])[C:4]([OH:5])=[O:3])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54760676N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

Product 1

HCID 451223662,4-Thiazolidinedicarboxylic acid, 3-acetyl-2-methyl-Yield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The crude product (10.19 g) of N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester, which was obtained by a method similar to that in Synthetic Example 13, was dissolved in ethanol (20 ml), and 4N NaOH was added thereto. The mixture was stirred under an argon atmosphere, and ethanol was added thereto to give a pale-yellow solid. The obtained solid was collected by filtration to give N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2Na salt (trans form) as crystals (9.09 g, about 72%).

Workup

  1. customto give a pale-yellow solid
  2. filtrationThe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-c1d38f46b4394190babe09992a69420b
Source dataset
uspto-grants-2015_12
Patent number
US09212154B2

Reaction notes

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