Lithium hydroxide, monohydrate → 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid

HRID 423031

반응식

HRID 423031 반응식
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([O:30]CC)=[O:29])[CH2:18][CH2:17][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.C(O)C.CCOC(C)=O>[C:4]([O:8][C:9]([NH:11][CH2:12][C:13]1([C:28]([OH:30])=[O:29])[CH2:14][CH2:15][N:16]([C:19]2[C:20]3[CH:27]=[CH:26][NH:25][C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:17][CH2:18]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

참가 물질

7

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 57750296ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2회

생성물 1

HCID 446042214-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid수율 63.1%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

Lithium hydroxide monohydrate (0.556 g, 13.26 mmol) was added to ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 11) (1.07 g, 2.65 mmol) in water (6.25 ml), THF (25 ml) and ethanol (25.00 ml). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×50 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (0.628 g, 63.1%) as a white foam.

후처리

  1. washwashed with water (20 mL)
  2. extractionthen extracted with EtOAc (3×50 mL)
  3. washThe organic extracts were washed with saturated brine (25 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-61da7afaeaaf4b2d9eafb3e4eca40de7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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