Water → O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

HRID 1351763Notes

Reaction equation

HRID 1351763 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH: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[O-].[Na+].CO.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CO>[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 23694274Sodium methanolate methanol

Product 1

HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-Boc-tyrosine (281 mg, 1.0 mmol) in methanol (0.5 mL) were added 28% sodium methoxide-methanol solution (0.42 mL, 2.1 mmol) and benzyl bromide (162 μL, 1.4 mmol), and the mixture was stirred at 40° C. for 3 hr. Then, water (2 mL) was added to make the system homogeneous, which system was analyzed by HPLC. As a result, the objective N-Boc-(O-benzyl)tyrosine (353 mg, conversion yield 95%) was confirmed.

Sources & evidence

ORD record
ord-b2745023eb2e4760b1bd495288144c9d
Source dataset
uspto-grants-2007_05
Patent number
US07217835B2

Reaction notes

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