Sodium Hydroxide → HCID 54153980, compound

HRID 439578Notes

Reaction equation

HRID 439578 reaction equation
C[N:2]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:3]([C:16]([OH:18])=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1.[OH-].[Na+]>C(O)C>[C:22]([O:21][C:19]([NH:2][C@H:3]([C:16]([OH:18])=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70116193HCID 70116193, compound

Product 1

HCID 54153980HCID 54153980, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a ethanol solution of methyl N-(t-butoxycarbonyl)-O-methyl-3-nitro-L-tyrosine(6.74 g) was added 1N sodiumhydroxide solution (25 ml) and was stirred for 2 hours at roomtemperature. The solvent was evaporated and water (70 ml) and 1Nhydrochloric acid solution (27.5 ml) was added, extracted with ethylacetate (50 ml×3). After ethyl acetate layer was washed withsaturated brine, the residue was dried over anhydrous sodiumsulfate. The solvent was evaporated in vacuo. To the residue wasadded hexane and ether and it was crystallized to give N-(t-butoxycarbonyl)-O-methyl-3-nitro-L-tyrosine (6.61 g).

Workup

  1. customThe solvent was evaporated
  2. additionwater (70 ml) and 1Nhydrochloric acid solution (27.5 ml) was added
  3. extractionextracted with ethylacetate (50 ml×3)
  4. washAfter ethyl acetate layer was washed
  5. dry with materialthe residue was dried over anhydrous sodiumsulfate
  6. customThe solvent was evaporated in vacuo
  7. customwas crystallized

Sources & evidence

ORD record
ord-5c70abe67f074a6a98b6ec51c645c2fd
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

Loading…