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

HRID 503709ノート

反応式

HRID 503709 の反応式
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]

参加物

6

反応物 3

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

生成物 2

HCID 13850981N-(tert-Butoxycarbonyl)-3-(dimethylamino)alanine収率 31%HCID 64796328HCID 64796328、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3-Dimethylamino-2-methylamino-propan-1-ol is prepared from 4-aza-DL-leucine 2HCl. Di-tert-butyl dicarbonate (0.65 g, 2.97 mmol) is added to a biphasic mixture of 4-aza-DL-leucine 2HCl (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 Na2SO4.10H2O. 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-1-ol as an oil.

後処理

  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)

出典と根拠

ORDレコード
ord-17755744f015448db739339ba1fa2e00
出典データセット
uspto-grants-2010_08
特許番号
US07777032B2

反応ノート

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