Acetic Anhydride → HCID 516558, compound

HRID 1611643Notes

Reaction equation

HRID 1611643 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][C:14](=[O:16])[CH3:15])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1.C(Cl)Cl>[C:1]([NH:4][C@H:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][C:14](=[O:16])[CH3:15])=[O:9])[CH2:6][S:7][C:17](=[O:19])[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 484333Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)ester

Product 1

HCID 516558HCID 516558, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution comprising 83 mg (0.31 mmol) of I-152 in 1 ml of pyridine is stirred at 0° C. and 90 μm (0.95 mmol) of acetic anhydride are added. The reaction mixture is maintained at 0° C. for 15 min, then it is allowed to return to ambient temperature and stirring is continued for 12 h. The solution is subsequently evaporated to dryness under vacuum and the residue formed is taken up in 30 ml of CH2Cl2. The organic phase is washed with water (3×20 ml), dried over sodium sulfate, filtered and evaporated to dryness under vacuum. The residual gum is crystallized from AcOEt and provides 73 mg (Yd=75%) of the expected compound in the form of colorless platelets. Rf (CH2Cl2/MeOH, 9.5/0.5): 0.46. M.p.=153-154° C. [α]D20=−33.7° (c 0.8, CHCl3).

Workup

  1. temperatureThe reaction mixture is maintained at 0° C. for 15 min
  2. customto return to ambient temperature
  3. stirringstirring
  4. customThe solution is subsequently evaporated to dryness under vacuum
  5. customthe residue formed
  6. washThe organic phase is washed with water (3×20 ml)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness under vacuum
  10. customThe residual gum is crystallized from AcOEt

Sources & evidence

ORD record
ord-5edd853dff974b9f8e783732eccf11ff
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

Loading…