Lithium hydroxide, monohydrate → Boc-DL-m-tyrosine

HRID 449505Notes

Reaction equation

HRID 449505 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 23033930Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate

Product 1

HCID 13890118Boc-DL-m-tyrosineYield 102.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate (0.91 g, 3.1 mmol) was taken up in methanol (30 mL) at rt and the lithium hydroxide monohydrate (0.51 g, 12.3 mmol) in water (10 mL) was added. The reaction was complete after stirring for 2 h. The methanol was removed under reduced pressure to give an aqueous layer which was partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoic acid (0.89 g, 100%). Analytical LCMS (M+H-Boc)+: m/z=181.9.

Workup

  1. customThe methanol was removed under reduced pressure
  2. customto give an aqueous layer which
  3. customwas partitioned between ethyl acetate and 1 N HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d6c65e0a4064808967edc0f5d56a948
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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