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Triethylamine → Methyl (s)-1-((s)-2-(2-diazoacetyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

HRID 1471020
ノート
印刷プレビュー

反応式

HRID 1471020 の反応式
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:17]([CH3:19])[CH3:18])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:16])=O)=[O:8])=[O:4].CCN(CC)CC.ClC(OCC(C)C)=O.[N+:35](=[CH2:37])=[N-:36]>O1CCCC1.CCOCC>[N+:35](=[CH:37][C:14]([C@@H:10]1[CH2:11][CH2:12][CH2:13][N:9]1[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:17]([CH3:19])[CH3:18])=[O:16])=[N-:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 12071044(S)-1-((S)-2-((Methoxycarbonyl)amino)-3-methylbutanoyl)pyrrolidine-2-carboxylic acid

生成物 1

HCID 131731308Methyl (s)-1-((s)-2-(2-diazoacetyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate収率 75%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of Example 37B (100 mg, 0.367 mmol) and Et3N (154 μL, 1.102 mmol) in tetrahydrofuran (4 mL) at 0° C. was added Isobutyl chloroformate (50 μL, 0.386 mmol). Mixture was then stirred at 0° C. for 30 minutes followed by addition of excess diazomethane in Et2O. Mixture was allowed to slowly come to ambient temperature over 3 hours. Mixture was then concentrated and diluted with EtOAc. Organic was then washed with saturated aqueous NaHCO3 and brine. Organic was dried (MgSO4), filtered and concentrated. Purification by chromatography (silica gel, 100% EtOAc) afforded 82 mg (75%) of the title compound. MS (ESI) m/z 297 (M+H)+.

後処理

  1. waitto slowly come to ambient temperature over 3 hours
  2. concentrationMixture was then concentrated
  3. additiondiluted with EtOAc
  4. washOrganic was then washed with saturated aqueous NaHCO3 and brine
  5. dry with materialOrganic was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica gel, 100% EtOAc)

出典と根拠

ORDレコード
ord-f6aac5a412524792840bbaa0034f2b6c
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006387B2

反応ノート

読み込み中…

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