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Diisopropylethylamine → (3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester

HRID 49700
ノート
印刷プレビュー

反応式

HRID 49700 の反応式
F[C:2](F)(F)[C:3](O)=O.[C:8]1([CH3:40])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1N[C:17]2[CH:23]=[C:22]([CH2:24][C:25]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([CH:34]([CH3:39])[CH2:35][C:36]([OH:38])=[O:37])=[N:32][CH:33]=3)=[O:26])[CH:21]=[CH:20][C:18]=2[N:19]=1.F[P-](F)(F)(F)(F)F.N1([O:57]C(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.NC1C=CC(C(C)CC(OCC)=O)=NC=1>CN(C)C=O>[CH2:2]([O:38][C:36](=[O:37])[CH2:35][CH:34]([C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:25](=[O:26])[CH2:24][C:22]2[CH:21]=[CH:20][C:18]3[N:19]=[C:15]([NH:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[CH3:40])[O:57][C:17]=3[CH:23]=2)=[CH:33][N:32]=1)[CH3:39])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9829176(3RS)-3-{5-[2-(2-o-Tolylamino-3H-benzimidazol-5-yl)-acetylamino]-pyridin-2-yl}-butyric acid trifluoroacetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17946645ethyl (3RS)-3-(5-aminopyrid-2-yl)butyrate

生成物 1

HCID 9890975
(3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester
収率 140.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A stirred solution of 2-o-tolylamino-benzoxazol-6-acetic acid (0.42 g, Reference Example 2) in dimethylformamide (15 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.57 g), then with diisopropylethylamine (0.4 g) and then with a solution of ethyl (3RS)-3-(5-aminopyrid-2-yl)butyrate (0.3 g, Reference Example 5) in dimethylformamide (5 mL). The mixture was stirred at room temperature for 5 hours then left to stand over night and then evaporated to low bulk. The residue was partitioned between water and ethyl acetate. The organic phase was washed with dilute acetic acid, then with water, then with aqueous bicarbonate solution (5%), then with water, then with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate to give the title compound (0.5 g) as a colourless glass. TLC: RF=0.36 (eluting with ethyl acetate). MS: 473 (MH+).

後処理

  1. waitthen left
  2. waitto stand over night
  3. customevaporated to low bulk
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with dilute acetic acid
  6. dry with materialwith water, then with aqueous bicarbonate solution (5%), then with water, then with brine, then dried
  7. customevaporated

出典と根拠

ORDレコード
ord-ab39d4a2592841388c2555f65dd8ac8e
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06706738B2

反応ノート

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