Acetic Anhydride → N-acetylpenicillamine, (L)-

HRID 875273

Reaction equation

HRID 875273 reaction equation
[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]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 92863L-Penicillamine

Product 1

HCID 164975N-acetylpenicillamine, (L)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-f8ede325c69544b0939cf9c8405e41ce
Source dataset
uspto-grants-2015_03
Patent number
US08981139B2

Linked notes

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