Acetic Anhydride → N-acetylpenicillamine, (L)-

HRID 875273

反応式

HRID 875273 の反応式
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]([C:14]([OH:16])=[O:15])[C:10]([SH:13])([CH3:12])[CH3:11]>N1C=CC=CC=1.C(O)C>[C:1]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[C:10]([SH:13])([CH3:12])[CH3:11])(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 92863L-Penicillamine

生成物 1

HCID 164975N-acetylpenicillamine, (L)-

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1049Pyridine溶媒

実験手順

Acetic anhydride (96 mmol, 9.80 g) was added dropwise to a well stirred solution of D-(−) penicillamine (40 mmol, 5.97 g) in pyridine (50 mL) at 0° C. After 30 min, the flask was removed from ice and allowed to stir at room temperature for 15 h. The resultant orange solution was partitioned between chloroform and dilute HCl and washed 4× with dilute HCl. After drying over MgSO4, the organic phase was evaporated to yield an orange residue. The residue was first dissolved in absolute ethanol (20 mL), and then precipitated in pentane at −78° C. The light yellow crystalline product was isolated by filtration (2.07 g, 30%). 1H NMR (CDCl3) δ 1.65 (s, CH3), 1.86 (s, CH3), 2.05 (s, NHCOCH3), 5.68-5.70 (d, CH(CH3)2), 6.56 (NHCOCH3). 13C NMR (CDCl3) δ 22.52 (NHCOCH3), 26.20 (CH(CH3)2), 30.22 (CH(CH3)2), 51.23 (CH), 169.37 (NHCOCH3), 192.21 (SCO).

後処理

  1. customthe flask was removed from ice
  2. customThe resultant orange solution was partitioned between chloroform and dilute HCl
  3. washwashed 4× with dilute HCl
  4. dry with materialAfter drying over MgSO4
  5. customthe organic phase was evaporated
  6. customto yield an orange residue
  7. customprecipitated in pentane at −78° C
  8. customThe light yellow crystalline product was isolated by filtration (2.07 g, 30%)

出典と根拠

ORDレコード
ord-f8ede325c69544b0939cf9c8405e41ce
出典データセット
uspto-grants-2015_03
特許番号
US08981139B2

関連ノート

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