Triphenylphosphine → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid

HRID 229121노트

반응식

HRID 229121 반응식
[CH3:1][C:2](C)([CH2:7][C:8]1C=C[CH:11]=[C:10](O)[CH:9]=1)[C:3]([O:5]C)=[O:4].[C:16]1([CH:22]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:23][N:24]([CH2:37][CH2:38][CH2:39][OH:40])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(O[CH:77]([CH3:79])[CH3:78])=O)=O)C>C1COCC1.O>[C:41]1([CH:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[C:27]=2[Cl:36])[CH2:37][CH2:38][CH2:39][O:40][C:11]2[C:77]([CH3:78])([CH3:79])[CH:7]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:8]=[CH:9][CH:10]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olHCID 67520417Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate

생성물 1

HCID 68864466N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate (135 mg, 0.65 mmol) and N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-hydroxypropylamine (290 mg, 0.65 mmol) in THF (8 mL) was treated with Ph3P (170 mg, 0.65 mmol), diisopropylazodicarboxylate (135 mg, 0.65 mmol), and stirred for 16 h. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried, and concentrated. Purification via silica gel column chromatography eluted with 30% EtOAc:hexane yielded the titled compound (200 mg, 50%). MS (ESI) 639 (M+H+).

후처리

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O
  3. customdried
  4. concentrationconcentrated
  5. customPurification via silica gel column chromatography
  6. washeluted with 30% EtOAc

출처 및 근거

ORD 기록
ord-958175d07f5c4b8c9fbd1e1ffcded43c
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560586B2

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