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Ethanol → (2RS,4R)-2-(2,4-dihydroxyphenyl)thiazolidine-4-carboxylic acid

HRID 338781
Notes
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Reaction equation

HRID 338781 reaction equation
C(O)C.[OH:4][C:5]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:6]=1[CH:7]=O.O.Cl.[NH2:16][C@H:17]([C:20]([OH:22])=[O:21])[CH2:18][SH:19].C([O-])(=O)C.[Na+]>O>[OH:4][C:5]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:6]=1[CH:7]1[NH:16][C@H:17]([C:20]([OH:22])=[O:21])[CH2:18][S:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 72132,4-DihydroxybenzaldehydeHCID 23462L-Cysteine hydrochloride monohydrateHCID 517045Sodium Acetate

Product 1

HCID 60194536(2RS,4R)-2-(2,4-dihydroxyphenyl)thiazolidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

In a mixed solvent including ethanol (10 ml) and water (10 ml), a solution including 2,4-dihydroxybenzaldehyde (943 mg, 6.83 mmol), L-cysteine hydrochloride monohydrate (1.0 g, 5.69 mmol), and sodium acetate (495 mg, 6.03 mmol) was stirred at room temperature for 14 hours. The produced precipitate was filtered, and a filter cake was washed with water, and ethyl acetate to obtain the target product that is a solid white (1.316 g, 95.8%).

Workup

  1. filtrationThe produced precipitate was filtered
  2. washa filter cake was washed with water, and ethyl acetate
  3. customto obtain the target product that

Sources & evidence

ORD record
ord-9299a74564c14a0f848dd393c14e3a7c
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes