Triphenylphosphine → 3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride salt

HRID 229097ノート

反応式

HRID 229097 の反応式
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([OH:11])[CH:5]=1.[C:13]1([CH:19]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:20][N:21]([CH2:34][CH2:35][CH2:36]O)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[C:24]=2[Cl:33])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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>C1(C)C=CC=CC=1>[ClH:33].[Cl:33][C:24]1[C:25]([C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][N:21]([CH2:20][CH:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:34][CH2:35][CH2:36][O:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH3:10])[C:3]([OH:2])=[O:12]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 354091Methyl 3-hydroxy-4-methylbenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

生成物 1

HCID 688622453-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride salt収率 103.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a stirring solution of 3-hydroxy-4-methyl-benzoic acid methyl ester (102 mg, 0.61 mmol) in anhydrous toluene (5 mL) was added N-(2,2-diphenylethyl)-N-(3-hydroxy-propyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (211 mg, 0.47 mmol). Polymer bound triphenylphosphine (250 mg, 0.75 mmol, 3 mmol/g, Fluka Chemie) was then added, and the mixture stirred for 15 minutes. The reaction mixture was then cooled to 0° C. and diisopropylazodicarboxylate (115 ul, 0.58 mmol) was added in a dropwise fashion. After stirring at room temperature overnight, the crude reaction mixture was filtered and the resulting solid was washed with toluene. The filtrate was concentrated and the crude product was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm) to give 150 mg (54% yield) of the title compound as a viscous oil. MS(ESI) 596.0(M+).

後処理

  1. additionwas then added
  2. stirringAfter stirring at room temperature overnight
  3. customthe crude reaction mixture
  4. filtrationwas filtered
  5. washthe resulting solid was washed with toluene
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile: H2O, UV detection at 254 nm)

出典と根拠

ORDレコード
ord-a9595c475e134ad5a39e07c081880178
出典データセット
uspto-grants-2009_07
特許番号
US07560586B2

反応ノート

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