Dimethylamine → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627164노트

반응식

HRID 627164 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[C:11]([C:23](O)=[O:24])[C@H:10]([OH:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][NH:28][CH3:29].C1COCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Si:16]([O:15][CH2:14][C@@H:13]1[CH:12]=[C:11]([C:23](=[O:24])[N:28]([CH3:29])[CH3:27])[C@H:10]([OH:26])[CH2:9][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

참가 물질

7

반응물 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89851992(3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acid2회

생성물 1

HCID 89851842(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acid (Intermediate 136, 4.07 g, 10.50 mmol) in DMF (20 mL) at room temperature was added 2M dimethylamine in THF (5.25 mL, 10.50 mmol), HATU (5.99 g, 15.75 mmol) and then DIEA (5.50 mL, 31.51 mmol). The reaction mixture was stirred at room temperature. The reaction ran until the starting material was consumed, then it was quenched with water and extracted with EtOAc. The organic solutions was then washed with brine, and purified via flash chromatography (35-100% EA/Hex) to isolate the desired product (3.05 g, 70.0%) as a pink glassy solid.

후처리

  1. customwas consumed
  2. customit was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic solutions was then washed with brine
  5. custompurified via flash chromatography (35-100% EA/Hex)

출처 및 근거

ORD 기록
ord-10f70fc317eb48e690644e7ed846fffe
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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