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

HRID 423031

反応式

HRID 423031 の反応式
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]

参加物

7

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 57750296ethyl 4-((tert-butoxycarbonylamino)methyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-61da7afaeaaf4b2d9eafb3e4eca40de7
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

関連ノート

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