Acetic Anhydride → HCID 86679522, compound

HRID 1776566Notes

Reaction equation

HRID 1776566 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([SH:16])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[C:19](OC(=O)C)(=[O:21])[CH3:20]>O>[C:19]([S:16][C:13]([CH3:15])([CH3:14])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]([OH:12])=[O:11])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 10467248158944-97-9

Product 1

HCID 86679522HCID 86679522, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

2-(tert-butoxycarbonylamino)-3-mercapto-3-methylbutanoic acid (2.96 g, 11.87 mmol) was suspended in water (33 ml) and cooled with an ice/water bath. KOH (1.67 g, 29.7 mmol) dissolved in water (16 ml) followed by acetic anhydride (1.41 ml, 14.9 mmol) were added to the reaction flask and stirred at 0-5° C. for 4 hours (a white precipitated appears after ca. 30 minutes of stirring). The reaction mixture was partitioned between EtOAc and HCl 1M. The aqueous layer was extracted 3 times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4, filtered and solvent removed under vacuum. Crude compound was used in the next step without further purification. (3.45 g, quantitative yield).

Workup

  1. temperaturecooled with an ice/water bath
  2. additionwere added to the reaction flask
  3. customa white precipitated
  4. waitappears after ca. 30 minutes
  5. stirringof stirring)
  6. customThe reaction mixture was partitioned between EtOAc and HCl 1M
  7. extractionThe aqueous layer was extracted 3 times with EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customsolvent removed under vacuum
  12. customCrude compound was used in the next step without further purification

Sources & evidence

ORD record
ord-fabde47d2b634ca7ae183a4ec036e8da
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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