Hydrochloric Acid → (alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid

HRID 716528

反応式

HRID 716528 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[CH3:17][O:18][C:19](Cl)=[O:20].Cl>O1CCCC1.O>[CH3:17][O:18][C:19]([NH:11][C@H:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:8]([OH:10])=[O:9])=[O:20]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 70134Phenylglycine, D-HCID 516892Sodium Bicarbonate

生成物 1

HCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acid収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

D-(−)-α-Phenylglycine (0.165 mmol) was dissolved in tetrahydrofuran (500 mL), followed by the addition of NaHCO3 (0.496 mmol) in water (500 mL), and then the addition of methylchloroformate (0.182 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. The mixture was acidified to pH=3 with HCl (1N) and the volatile was concentrated in vacuo. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give compound 31 as a pale yellow solid in 80% yield. MS (ESI, EI+) m/z=209 (MH+).

後処理

  1. concentrationthe volatile was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d29ace45e3554fff8245c4da1b951547
出典データセット
uspto-grants-2015_11
特許番号
US09187496B2

関連ノート

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