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

HRID 229121ノート

反応式

HRID 229121 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-958175d07f5c4b8c9fbd1e1ffcded43c
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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