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

HRID 923660

반응식

HRID 923660 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0d8322577e0848fcbf4e8f05bf79edc5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278978B2

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