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Diisopropylethylamine → HCID 71197908、化合物

HRID 2415542
ノート
印刷プレビュー

反応式

HRID 2415542 の反応式
C(N(CC)C(C)C)(C)C.Cl.[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17](C(O)=O)[CH2:16]1)([CH3:14])([CH3:13])[CH3:12].Cl.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:44]2[CH2:45][CH2:46][NH:47][CH2:48][CH:49]=2)=[C:37]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:38]=1.F[P-](F)(F)(F)(F)F.N1([O:66][C:67](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17]([C:67]([N:47]2[CH2:46][CH:45]=[C:44]([C:36]3[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][C:37]=3[CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:49][CH2:48]2)=[O:66])[CH2:16]1)([CH3:12])([CH3:14])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67212109(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochlorideHCID 86590371HCID 86590371、化合物

生成物 1

HCID 71197908HCID 71197908、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N,N-diisopropylethylamine (1.36 mL, 7.80 mmol) was added to a stirred suspension of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid (1-7) (0.831 g, 2.60 mmol), methyl [5-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]acetate hydrochloride (1-6) (0.690 g, 2.60 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.19 g, 3.12 mmol) and 1-hydroxy-7-azabenzotriazole (0.425 g, 3.12 mmol) in N,N-dimethylformamide (5.2 mL) at ambient temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent) provided 1-8 as a pale yellow oil (m/z (ES) 531 (MH+).

後処理

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent)

出典と根拠

ORDレコード
ord-d907e828abaa47ddb437d0fe469e85ac
出典データセット
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06818658B2

反応ノート

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