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

HRID 902716노트

반응식

HRID 902716 반응식
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([O:38][CH3:39])=[O:37].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[C:26]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][O:25][C:33]2[CH:42]=[CH:41][CH:40]=[C:35]([C:36]([O:38][CH3:39])=[O:37])[CH:34]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[C:12]=2[Cl:21])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

생성물 1

HCID 577571333-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester수율 26%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-hydroxypropylamine (186 mg, 0.42 mmole) and methyl 3-hydroxybenzoate (63 mg, 0.42 mmole) in 15 mL of THF was treated with Ph3P (110 mg, 0.42 mmole) and diisopropylazodicarboxylate (93 mg, 0.46 mmole). The reaction was stirred for 18 hours, diluted with H2O, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent evaporated. The residue was chromatographed on a silica gel column, and elution with 10% EtOAc in hexane gave the titled product, 64 mg (26% yield). MS (ESI) 583 (MH+).

후처리

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was chromatographed on a silica gel column, and elution with 10% EtOAc in hexane

출처 및 근거

ORD 기록
ord-9b8dac70c19241308030bc732178d057
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365085B2

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