Propylphosphonic anhydride → (1-{4-Bromo-6-[(triisopropylsilanyl)-ethynyl]-pyridin-2-ylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

HRID 923660ノート

反応式

HRID 923660 の反応式
C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.[Br:19][C:20]1[CH:25]=[C:24]([C:26]#[C:27][Si:28]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])[N:23]=[C:22]([NH2:38])[CH:21]=1.[CH3:39][N:40]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH:41]([CH3:45])[C:42](O)=[O:43].C(=O)([O-])O.[Na+]>CCOC(C)=O.N1C=CC=CC=1>[C:49]([O:48][C:46](=[O:47])[N:40]([CH:41]([C:42](=[O:43])[NH:38][C:22]1[CH:21]=[C:20]([Br:19])[CH:25]=[C:24]([C:26]#[C:27][Si:28]([CH:32]([CH3:34])[CH3:33])([CH:35]([CH3:37])[CH3:36])[CH:29]([CH3:31])[CH3:30])[N:23]=1)[CH3:45])[CH3:39])([CH3:50])([CH3:51])[CH3:52]

参加物

7

反応物 4

HCID 111923Propylphosphonic anhydrideHCID 516892Sodium BicarbonateHCID 44368572-(((Tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 1233890784-Bromo-6-[2-[tris(propan-2-yl)silyl]ethynyl}pyridin-2-amine

生成物 1

HCID 123968434(1-{4-Bromo-6-[(triisopropylsilanyl)-ethynyl]-pyridin-2-ylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (70 ml of a 50 wt.-% solution in EtOAc, 118 mmol) is added to a mixture of 4-bromo-6-{2-[tris(propan-2-yl)silyl]ethynyl}pyridin-2-amine B1 (10.4 g, 29.5 mmol), 2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid (12 g, 59 mmol) and pyridine (20 ml) at −20° C. The mixture is stirred for 3 h at that temperature. 200 ml of a saturated aqueous sodium hydrogencarbonate solution is added and the mixture extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 11.1 g (70%). HPLC-MS: M+H=538/540; tR=.2.05 min (METHOD—1).

後処理

  1. extractionthe mixture extracted with EtOAc
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by NP chromatography
  5. custom2.05 min (METHOD—1)

出典と根拠

ORDレコード
ord-0d8322577e0848fcbf4e8f05bf79edc5
出典データセット
uspto-grants-2016_03
特許番号
US09278978B2

反応ノート

読み込み中…