Hydrochloric Acid → 2-[3-(2-m-Tolyl-ethoxy)-4-trifluoromethyl-benzoylamino]-indane-2-carboxylic acid methyl ester

HRID 521482ノート

反応式

HRID 521482 の反応式
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([O:26][C:27](=O)[CH3:28])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:38][C:39]1[CH:40]=[C:41](CCO)[CH:42]=[CH:43][CH:44]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CO>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[C:18]([O:26][CH2:27][CH2:28][C:43]3[CH:44]=[C:39]([CH3:38])[CH:40]=[CH:41][CH:42]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 746483-MethylbenzeneethanolHCID 5363146Diisopropyl azodicarboxylateHCID 670766942-(3-Acetoxy-4-trifluoromethyl-benzoylamino)-indane-2-carboxylic acid methyl ester

生成物 1

HCID 670766442-[3-(2-m-Tolyl-ethoxy)-4-trifluoromethyl-benzoylamino]-indane-2-carboxylic acid methyl ester収率 43.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

200 mg (0.48 mmol) of the compound of step 2 were dissolved in 5 ml of methanol, 13.1 mg (0.1 mmol) of potassium carbonate were added and the mixture was stirred for 30 min. The mixture was acidified with 1 N hydrochloric acid and extracted three times with 20 ml portions of EA. The combined organic phases were dried and evaporated. The residue was dissolved in 5 ml of THF, 96.9 mg (0.71 mmol) of 2-(3-methylphenyl)-ethanol and 186.7 mg (0.71 mmol) of triphenylphosphine were added, the mixture was cooled in an ice bath, and 191.9 mg (0.95 mmol) of DIAD were added. After stirring overnight, the mixture was evaporated to dryness and the residue was purified by preparative RP HPLC (water/ACN gradient). 104 mg of the title compound were obtained.

後処理

  1. extractionextracted three times with 20 ml portions of EA
  2. customThe combined organic phases were dried
  3. customevaporated
  4. dissolutionThe residue was dissolved in 5 ml of THF
  5. temperaturethe mixture was cooled in an ice bath
  6. stirringAfter stirring overnight
  7. customthe mixture was evaporated to dryness
  8. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

出典と根拠

ORDレコード
ord-192855ae54074177a7010b9501131f2b
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

反応ノート

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