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Lithium Hydroxide → 2-Acetamidooxazole-4-carboxylic acid

HRID 467469
Notes
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Reaction equation

HRID 467469 reaction equation
NC1OC=C(C(OCC)=O)N=1.CC(OC(C)=O)=O.[C:19]([NH:22][C:23]1[O:24][CH:25]=[C:26]([C:28]([O:30]CC)=[O:29])[N:27]=1)(=[O:21])[CH3:20].[Li+].[OH-]>CCO>[C:19]([NH:22][C:23]1[O:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)(=[O:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 7918Acetic AnhydrideHCID 2153734-Oxazolecarboxylic acid, 2-(acetylamino)-, ethyl esterHCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylate

Product 1

HCID 840118932-Acetamidooxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

1.0 g (6.41 mmol) ethyl 2-aminooxazole-4-carboxylate and 9.10 mL (96.3 mmol) Ac2O are stirred at r.t. over the weekend. Then the solvent is removed in vacuo. Some toluene is added and all volatile components are removed in vacuo again. This procedure is repeated three times. The crude product is used without further purification. b) 1.31 g (6.60 mmol) of ethyl 2-acetamidooxazole-4-carboxylate are added to 33 mL EtOH. 0.55 g (13.2 mmol) LiOH are added and the resulting mixture is stirred at r.t. over night. Then the EtOH is removed in vacuo and diluted aq. HCl is added and the resulting precipitate is collected, washed with cold water and dried. The resulting product is used without further purification.

Workup

  1. customThen the solvent is removed in vacuo
  2. additionSome toluene is added
  3. customall volatile components are removed in vacuo again
  4. customThe crude product is used without further purification
  5. customThen the EtOH is removed in vacuo and diluted aq. HCl
  6. additionis added
  7. customthe resulting precipitate is collected
  8. washwashed with cold water
  9. customdried
  10. customThe resulting product is used without further purification

Sources & evidence

ORD record
ord-79ab2ff40fbf4f85b71afd236327c6fb
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08623860B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes