L-Tyrosine → HCID 54333393, compound

HRID 2103938Notes

Reaction equation

HRID 2103938 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16]>[OH-].[Na+]>[CH2:18]([O:17][C:15]([NH:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:16])[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 6057L-TyrosineHCID 18052Allyl chloroformate

Product 1

HCID 54333393HCID 54333393, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of tyrosine (10 g) in 4N aq. sodium hydroxide (30 mL) cooled in an ice bath was slowly added allyl chloroformate (6.4 mL) in a period of 20 minutes. Ten minutes after completion of the addition the ice bath was removed and 4N aq. sodium hydroxide (30 mL) and H2O (5mL) were added. After two hours at RT MeOH (60 mL) was added. After an additional two hours the reaction mixture was extracted with Et2O. The aq. mixture was cooled in an ice bath, acidified to pH 2-3 using 36-38% hydrochloric acid and extracted with EtOAc. De organic extract was dried (Na2SO4) and concentrated under reduced pressure to give Alloc-Tyr-OH (38) as an oil (14.5 g, 88%). Rf 0.35 (DCM/MeOH/AcOH, 89/10/1, v/v/v).

Workup

  1. customof 20 minutes
  2. customwas removed
  3. addition4N aq. sodium hydroxide (30 mL) and H2O (5mL) were added
  4. additionAfter two hours at RT MeOH (60 mL) was added
  5. extractionAfter an additional two hours the reaction mixture was extracted with Et2O
  6. temperatureThe aq. mixture was cooled in an ice bath
  7. extractionextracted with EtOAc
  8. extractionDe organic extract
  9. dry with materialwas dried (Na2SO4)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bfd4824122b43948f2b7def6405bed5
Source dataset
uspto-grants-2009_08
Patent number
US07576071B2

Reaction notes

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