Hydrochloric Acid → 1-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid

HRID 557877Notes

Reaction equation

HRID 557877 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:18][C:19]([NH2:21])=[O:20].C(O)C.[OH-].[Li+].Cl>C(OCC)(=O)C.CO.C1COCC1>[NH2:21][C:19]1[O:20][CH:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([C:11]3([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]3)=[CH:9][CH:10]=2)[N:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 3939Lithium HydroxideHCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Product 1

HCID 666616511-[4-(2-Amino-1,3-oxazol-4-yl)phenyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl 1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate (0.20 g, 0.00079 mol, example 243, steps 1 & 2) and urea (0.095 g, 0.0016 mol) in ethanol (5.0 mL, 0.086 mol) was refluxed overnight. The mixture was diluted with ethyl acetate and washed with sat'd. NaHCO3, brine, dried and concentrated. The methyl ester was purified by CombiFlash using CH2Cl2/EtOAc (max. EtOAc 100%). The ester was hydrolyzed using lithium hydroxide (6.0 eq.) in methanol/THF and then acidified by adding 1 N HCl. The solvent was removed under vacuum and the crude product was used in the next step. LC-MS: 259.2 (M+H+) methyl eater; 245.2 (M+H+) acid

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with sat'd
  3. dry with materialNaHCO3, brine, dried
  4. concentrationconcentrated
  5. customThe methyl ester was purified by CombiFlash
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-900a02d7354b4fb0a463c27cf0f3a26c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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