Sodium Hydroxide → 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid

HRID 423081

反応式

HRID 423081 の反応式
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([O:41]C)=[O:40])[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:28][CH2:27]4)=[CH:24][N:23](S(C4C=CC(C)=CC=4)(=O)=O)[C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1.CCOC(C)=O>[C:3]([O:7][C:8]([NH:10][C:11]1([C:39]([OH:41])=[O:40])[CH2:12][CH2:13][N:14]([C:17]2[C:18]3[C:25]([CH:26]4[CH2:27][CH2:28]4)=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:15][CH2:16]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 57750287methyl 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate2 回

生成物 1

HCID 577503464-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid収率 68.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

2M sodium hydroxide solution (5.00 mL) was added to methyl 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylate (Intermediate 63) (780 mg, 1.37 mmol) in THF (10 mL) at 20° C. The resulting solution was stirred at 40° C. for 24 hours. The reaction mixture was diluted with EtOAc (50 mL) and the aqueous layer was collected and acidified to pH4 with 2M HCl solution. The aqueous layer was extracted with DCM (2×50 mL) and the organic layers combined and washed with saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product 4-(tert-butoxycarbonylamino)-1-(5-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (375 mg, 68.2%) as a cream solid.

後処理

  1. customthe aqueous layer was collected
  2. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  3. washwashed with saturated brine (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-a11ccb64ed894fcd90c8962c38b2578b
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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