Lithium hydroxide, monohydrate → 1-(tert-Butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid

HRID 423084노트

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HRID 423084 반응식
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][C:12]1([C:25]([O:27]C)=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.CO.CCOC(C)=O>[C:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][C:12]([NH:11][C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])([C:25]([OH:27])=[O:26])[CH2:17][CH2:16]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

참가 물질

7

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 577503561-Tert-butyl 4-methyl 4-(tert-butoxycarbonylamino)piperidine-1,4-dicarboxylate2회

생성물 1

HCID 12682251-(tert-Butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid수율 78%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
20 °C

실험 절차

Lithium hydroxide monohydrate (8.13 g, 193.62 mmol) was added to 1-tert-butyl 4-methyl 4-(tert-butoxycarbonylamino)piperidine-1,4-dicarboxylate (Intermediate 69) (13.88 g, 38.72 mmol) in water (21.51 mL), THF (86 mL) and methanol (86 mL). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (75 mL) and washed with water (75 mL). The aqueous was adjusted to pH5 with 1M citric acid solution, then extracted with EtOAc (3×200 mL). The organic extracts were washed with saturated brine (50 mL), then dried over MgSO4, filtered and evaporated to afford desired product 1-(tert-butoxycarbonyl)-4-(tert-butoxycarbonylamino)piperidine-4-carboxylic acid (10.36 g, 78%) as a fine white solid.

후처리

  1. washwashed with water (75 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe organic extracts were washed with saturated brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-0232f0a19c67453e81abacbe2e78a0b4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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