Acetic Anhydride → HCID 59909957, compound

HRID 1018265Notes

Reaction equation

HRID 1018265 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([NH2:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:4]([O:3][C:1]([NH:8][C@H:9]([C:18](=[O:19])[NH2:20])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:21](=[O:23])[CH3:22])=[CH:15][CH:16]=1)=[O:2])([CH3:5])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11022297HCID 11022297, compound

Product 1

HCID 59909957HCID 59909957, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Boc-tyrosine amide (0.960 g, 3.4 mmol) in pyridine (10 mL) stirred under argon was added acetic anhydride (808 μL, 8.56 mmol). After 18 hrs of stirring the solvent was evaporated, the residue taken in EtOAc (30 mL) washed with 5% aqueous citric acid (3×20 mL) and brine. The solution was dried (MgSO4) and the solvent evaporated to yield 949 mg (86%) of the title compound.

Workup

  1. customwas evaporated
  2. washwashed with 5% aqueous citric acid (3×20 mL) and brine
  3. dry with materialThe solution was dried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-f0be0889432b42b4824742af00cfc52e
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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