Acetic Anhydride → N-acetylpenicillamine, (L)-

HRID 875273

반응식

HRID 875273 반응식
[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]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 92863L-Penicillamine

생성물 1

HCID 164975N-acetylpenicillamine, (L)-

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1049Pyridine용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-f8ede325c69544b0939cf9c8405e41ce
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981139B2

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