3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 3-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester

HRID 473593

反応式

HRID 473593 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:10](=[O:20])[CH2:9]1)=O)(C)(C)C.[C:21]([N:28]1[CH2:31]C(=O)[CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.ClCCCl.CC(O)=O>[C:24]([O:23][C:21]([N:28]1[CH2:31][CH:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[CH:16][CH:17]=[CH:18][N:19]=3)[C:10](=[O:20])[CH2:9]2)[CH2:29]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

参加物

8

反応物 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 668236883-Oxo-4-pyrimidin-2-yl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 668362493-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester収率 10.5%

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of intermediate 3b (120 mg, 0.43 mmol) in TFA (0.75 mL) and CH2Cl2 (3 mL) was stirred at room temperature for 1.5 h. The solution was concentrated. The resulting residue was stirred with N-Boc-azetidin-3-one 1a (81 mg, 0.47 mmol) and Na(OAc)3BH (100, 0.47 mmol) in 1,2-dichloroethane (4 mL) and HOAc (0.2 mL) at room temperature overnight. The reaction was quenched with aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave intermediate 3c as light yellow solid (15 mg).

後処理

  1. concentrationThe solution was concentrated
  2. customThe reaction was quenched with aq. NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 3% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-e2272eb4ff46483387dd6f0643ba0185
出典データセット
uspto-grants-2014_01
特許番号
US08637498B2

関連ノート

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