Dimethyl Sulfoxide → Methyl 2-[(tert-butoxycarbonyl)amino]-2-methyl-3-oxopropanoate

HRID 2306880ノート

反応式

HRID 2306880 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([NH:18][C@:19]([CH3:26])([C:22]([O:24][CH3:25])=[O:23])[CH2:20][OH:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[C:11]([O:15][C:16]([NH:18][C:19]([CH3:26])([CH:20]=[O:21])[C:22]([O:24][CH3:25])=[O:23])=[O:17])([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10513799(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-methylpropanoate

生成物 1

HCID 22630101Methyl 2-[(tert-butoxycarbonyl)amino]-2-methyl-3-oxopropanoate収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of oxalyl chloride (2.93 g, 0.0231 mol) in CH2Cl2 (30 mL) at −60° C. was added DMSO (3.6 g, 0.0462 mol) during which the reaction temperature rose up to −55° C. The reaction mixture was stirred at this temperature for 10 min. before the addition of a solution of the methyl N-(tert-butoxycarbonyl)-2-methylserinate product of Example 1b (2.7 g, 0.01157 mol) in CH2Cl2 (20 mL) at −60° C. The reaction mixture was stirred for additional 20 min., quenched with Et3N (5.85 g, 0.0578 mol) between −60° C. to −30° C. and filtered. DI water (50 mL) and EtOAc (100 mL) were added to the filtrate and the layers were separated. The organic layer was dried over anhydrous MgSO4, filtered through Celite and concentrated on a rotovap to give the crude product as an yellow oil. This material was purified by column chromatography using 30% EtOAc in hexane as eluent to give the title product (yield 1.39 g, 49%).

後処理

  1. customrose up to −55° C
  2. filtrationfiltered
  3. additionDI water (50 mL) and EtOAc (100 mL) were added to the filtrate
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered through Celite
  7. concentrationconcentrated on a rotovap
  8. customto give the crude product as an yellow oil
  9. customThis material was purified by column chromatography

出典と根拠

ORDレコード
ord-a576dacbaf3f470290666cd02f422521
出典データセット
uspto-grants-2004_12
特許番号
US06828456B2

反応ノート

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