Pivalic acid → 1-(2-((4R,6R)-6-(2-(diphenylamino)-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

HRID 1608804ノート

反応式

HRID 1608804 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]([C:20](=O)[CH:21]([CH3:23])[CH3:22])[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:12])=[CH:4][CH:3]=1.[NH2:32][CH2:33][CH2:34][C@H:35]1[O:40][C:39]([CH3:42])([CH3:41])[O:38][C@@H:37]([CH2:43][C:44]([N:46]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:45])[CH2:36]1.CCCCCCC.C(O)(=O)C(C)(C)C>C1(C)C=CC=CC=1.O1CCCC1>[C:53]1([N:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:44](=[O:45])[CH2:43][C@@H:37]2[O:38][C:39]([CH3:42])([CH3:41])[O:40][C@H:35]([CH2:34][CH2:33][N:32]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[C:9]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:10]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[O:12])=[C:20]3[CH:21]([CH3:23])[CH3:22])[CH2:36]2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

参加物

7

反応物 4

HCID 6417Pivalic acidHCID 8900HeptaneHCID 99098724-(4-Fluorophenyl)-2-(2-methyl-1-oxopropyl)-4-oxo-3,N-diphenylbutanamideHCID 109486112-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-N,N-diphenylacetamide

生成物 1

HCID 111255291-(2-((4R,6R)-6-(2-(diphenylamino)-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A nitrogen purged 500 mL three-neck flask is charged with 4-fluoro-α-(2-methyl-1-oxopropyl)-γ-oxo-N,β-diphenylbenzenebutanamide (Baumann, supra) (13.6 g, 0.032 mol), (4R-cis)-6-(2-aminoethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide (10.0 g, 0. 027 mol), heptane (100 mL), pivalic acid (3 g), tetrahydrofuran (50 mL), and toluene (60 mL). The mixture is heated to reflux for 48 hours, cooled to room temperature, and diluted with toluene (300 mL). The solution is washed with 0.5N aqueous sodium hydroxide (150 mL), followed by 0.5N aqueous hydrochloric acid (250 mL), and concentrated by vacuum distillation to a foam. The product, (4R-cis)-1-[2-[6-[2-(diphenylamino)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-(4-fluorophenyl)-2-(1-methyl ethyl)-N,4-diphenyl-1H-pyrrole-3 -carboxamide, is used in the next step without further purification. Fourier Transform Infrared Spectroscopy (FTIR) (KBr) 3450, 2860, 1650, 1620 cm-1 ;

後処理

  1. customA nitrogen purged 500 mL three-neck flask
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 48 hours
  4. washThe solution is washed with 0.5N aqueous sodium hydroxide (150 mL)
  5. concentrationconcentrated by vacuum distillation to a foam
  6. customThe product, (4R-cis)-1-[2-[6-[2-(diphenylamino)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]ethyl]-5-(4-fluorophenyl)-2-(1-methyl ethyl)-N,4-diphenyl-1H-pyrrole-3 -carboxamide, is used in the next step without further purification

出典と根拠

ORDレコード
ord-7430b80a863940b59a5c0adc399abf35
出典データセット
uspto-grants-1995_03
特許番号
US05397792

反応ノート

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