Hydrochloric Acid → (+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid

HRID 1168437ノート

反応式

HRID 1168437 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:24]=4[C:25]([O:27]C)=[O:26])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>CC(O)(C)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58681954Methyl cis-2-(3-(2-(4-fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoate

生成物 1

HCID 59094663(+)-cis-2-(3-(2-(4-Fluorophenyl)oxazol-4-ylmethoxy)cyclohexyloxymethyl)-6-methylbenzoic Acid

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4.2 g (9.2 mmol) of 5b were dissolved in 120 ml of t-BuOH. 50 ml of 50% aq. KOH were added, and the mixture was then boiled at 100° C. for 24 hours. For work-up, the mixture was allowed to cool and then diluted with 100 ml of ethyl acetate. The aqueous phase was made slightly acidic by addition of 2 N aqueous HCl and extracted 2 more times with 100 ml of ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated, and the residue was purified by flash chromatography (methylene chloride/methanol/conc. ammonia, 30/5/1). This gave 6b as a white amorphous solid. TLC (methylene chloride/methanol/conc. ammonia, 30/5/1). Rf=0.3. Recrystallization from toluene. C25H26FNO5 (432.42) MS(ESI): 433 (M+H+).

後処理

  1. temperatureto cool
  2. extractionextracted 2 more times with 100 ml of ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (methylene chloride/methanol/conc. ammonia, 30/5/1)

出典と根拠

ORDレコード
ord-25b3d9d2e4984cd5b3d17c6d5e25e7ab
出典データセット
uspto-grants-2003_09
特許番号
US06624185B2

反応ノート

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