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

HRID 504340노트

반응식

HRID 504340 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-6e3ebcb8abbb40a783a0eb1eb4277d61
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776874B2

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