ChemicalBook CAS DataBase List O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER synthesis

9synthesis methods

Product Name:O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER
CAS Number:112196-58-4
Molecular formula:C22H37NO5Si
Molecular Weight:423.62

O-TERT-BUTYLDIMETHYLSILYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

112196-57-3
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74-88-4
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O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

112196-58-4
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Yield:112196-58-4 436 mg

Reaction Conditions:

Stage #1: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoatewith sodium hydride in tetrahydrofuran;N,N-dimethyl-formamide; for 0.166667 h;
Stage #2: methyl iodide in tetrahydrofuran;N,N-dimethyl-formamide; for 24 h;

Steps:

131.C Step C.

Step C.
Methyl (S)-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoate (Intermediate 131C)
Sodium hydride (72 mg, 1.80 mmol) was added to a solution of Intermediate 131B (692 mg, 1.69 mmol) in a mixture of THF (10 mL) and DMF (1 mL).
After stirring for 10 min, methyl iodide (316 mg, 5.08 mmol) was added and stirring was continued for 24 h.
The reaction mixture was partitioned between ethyl acetate (5 mL) and water (5 mL) and the organic layer was separated, washed with water (2*10 mL), dried (Na₂SO₄) and evaporated.
The product was purified on a Si cartridge (25 g) eluting with 0-25% ethyl acetate in cyclohexane to give the desired product as a yellow oil (436 mg). LCMS (Method 6): Rt=1.95 min, m/z 424.3 [M+H]⁺

References:

US2018/215758,2018,A1 Location in patent:Paragraph 0473

74-88-4
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$15.00/10g