Ammonia → (S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate

HRID 624885ノート

反応式

HRID 624885 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:32]1C=CC=CC=1.N>C(#N)C>[NH2:32][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]1[CH2:16][CH2:15]1

参加物

6

反応物 4

HCID 222AmmoniaHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 5706350(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

生成物 1

HCID 70082562(S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate収率 78%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (CAN 89483-06-7, 10 g, 44 mmol), di-tert-butyl dicarbonate (CAN:24424-99-5, 14.28 g, 66 mmol) and pyridine (2.4 mL) in acetonitrile (200 mL) was stirred at room temperature for 20 min. Ammonia (10 mL) was added dropwise for 20 min. The resulting reaction mixture was stirred for 4 h. During removal of most of the solvent under reduced pressure the product precipitated and the solid was filtered off and washed with acetonitrile (20 mL). The solid was dried under reduced pressure to give the title compound (7.73 g, 78%) as white solid; MS (EI): m/e 251.2 [M+Na]+.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 h
  3. customDuring removal of most of the solvent under reduced pressure the product
  4. customprecipitated
  5. filtrationthe solid was filtered off
  6. washwashed with acetonitrile (20 mL)
  7. customThe solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-3d6210924cbb44549b69d168bacf4b68
出典データセット
uspto-grants-2016_04
特許番号
US09303012B2

反応ノート

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