Glycine → (S)-2-Cyclopentyloxycarbonylamino-3,3-dimethyl-butyric acid

HRID 1015939

反応式

HRID 1015939 の反応式
[C:1](NCC(O)=O)([CH3:4])([CH3:3])[CH3:2].[C:10](=[O:25])(ON1C(=O)CCC1=O)[O:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C(=O)(O)[O-].[Na+].CC(C)=O>[CH:12]1([O:11][C:10]([NH:26][C@@H:27]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:28]([OH:30])=[O:29])=[O:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

参加物

6

反応物 3

HCID 750GlycineHCID 414246N-tert-ButylglycineHCID 15927743N-(Cyclopentyloxycarbonyloxy)succinimide

生成物 1

HCID 23595129(S)-2-Cyclopentyloxycarbonylamino-3,3-dimethyl-butyric acid収率 79%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

In a 5 L R flask dissolved t-butyl glycine (74 g, 0.56 mol, 1.02 eq.) in saturated sodium bicarbonate (11 vol). Cyclopentyl 2,5-dioxopyrrolidin-1-yl carbonate (126 g, 0.55 mol, 1 eq.) was dissolved in acetone (5.5 vol) and the solution slowly added via addition funnel at room temperature to the solution of the glycine. The reaction mixture was stirred at room temperature until complete (approximately 4 hours). The acetone was removed under reduced pressure and the remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each). The organic layers were discarded. The pH of the aqueous layer was adjusted to 2 with 2 N HCl and then extracted with ethyl acetate (thrice, 5.5 vol). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to provide a clear oil the slowly crystallized. The crude product was crystallized from hexanes/ethyl acetate to provide (S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid as a white solid (82 g). The mother liquid was stripped and a second crop of crystals obtained (combined yield 105.54 g, 79% yield).

後処理

  1. customThe acetone was removed under reduced pressure
  2. extractionthe remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each)
  3. extractionextracted with ethyl acetate (thrice, 5.5 vol)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto provide a clear oil the
  8. customslowly crystallized
  9. customThe crude product was crystallized from hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-f2ae958456cc49b48855dedbb8ea3261
出典データセット
uspto-grants-2011_07
特許番号
US07985762B2

関連ノート

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