Sodium Carbonate → N-(tert-Butoxycarbonyl)-3-(dimethylamino)alanine

HRID 1783603노트

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HRID 1783603 반응식
Cl.Cl.[NH2:3][CH:4]([C:9]([OH:11])=[O:10])[CH2:5][N:6]([CH3:8])[CH3:7].[C:12](O[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(OC(C)(C)C)=O.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[CH3:7][N:6]([CH3:8])[CH2:5][CH:4]([NH:3][CH3:12])[CH2:9][OH:11].[C:23]([O:22][C:20]([NH:3][CH:4]([CH2:5][N:6]([CH3:8])[CH3:7])[C:9]([OH:11])=[O:10])=[O:21])([CH3:24])([CH3:25])[CH3:26]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 441345533-(Dimethylamino)alanine--hydrogen chloride (1/2)2회

생성물 2

HCID 13850981N-(tert-Butoxycarbonyl)-3-(dimethylamino)alanine수율 31%HCID 64796328HCID 64796328, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-Dimethylamino-2-methylamino-propan-1-ol is prepared from 4-aza-DL-leucine 2 HCl. Di-tert-butyl dicarbonate (0.65 g, 2.97 mmol) is added to a biphasic mixture of 4-aza-DL-leucine 2 HCl (0.51 g, 2.47 mmol) in 10 ml 1:1 10% Na2CO3:MeCN. After stirring 16 hours, the MeCN is removed under reduced pressure and the aqueous layer is extracted with ethyl acetate. The aqueous layer is concentrated and purified by reverse phase column chromatography on a sep-pak C18 column (water) yielding 0.19 g (31%) 2-tert-butoxycarbonylamino-3-dimethylamino-propionic acid, sodium salt. The sodium salt is suspended in THF (5 ml) and cooled to 0° C. under N2. LAH (3.8 ml of a 1.0 M solution in THF) is added and the reaction mixture warmed to rt and than to reflux. After stirring at reflux for 16 h, the reaction mixture is cooled to 0° C. and carefully quenched by the slow addition of Na2SO4.10 H2O. The reaction mixture is diluted with diethyl ether, warmed to room temperature and stirred for 30 min. The gray suspension is filtered through Celite and the filtrate concentrated to give 83 mg (82%) of 3-dimethylamino-2-methylamino-propan-1ol as an oil.

후처리

  1. customthe MeCN is removed under reduced pressure
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. concentrationThe aqueous layer is concentrated
  4. custompurified by reverse phase column chromatography on a sep-pak C18 column (water)

출처 및 근거

ORD 기록
ord-87d9d2d9ebbd4c55aa6b5c61a5d99f8c
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501427B2

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