2',6'-dimethyl-beta-methyltyrosine

Base Information

• Chemical Name: 2',6'-dimethyl-beta-methyltyrosine
• CAS No.: 143739-15-5
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Mol file: 143739-15-5.mol

Synonyms:2’,6’-dimethyl-beta-methyltyrosine

Chemical Property of 2',6'-dimethyl-beta-methyltyrosine

Chemical Property:

• Boiling Point: 402.9°Cat760mmHg
• Flash Point: 197.5°C
• Density: 1.202g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',6'-dimethyl-beta-methyltyrosine

There total 32 articles about 2',6'-dimethyl-beta-methyltyrosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,5-dimethylmethoxybenzene (874-63-5) → (2R,3S) 2-amino-3-(2',6'-dimethyl-4'-hydroxyphenyl)butanoic acid (143739-15-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / Br₂ / CCl₄ / -25 °C

2: 1.) Mg / 1.) THF, reflux, 4 h, 2.) THF, 0 deg C to RT; RT, 1 h

3: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

4: LiOH*H₂O / methanol; H₂O

5: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

6: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

7: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

8: 96 percent / Amberlite IR/400 azide exchange resin / acetonitrile / 216 h / Ambient temperature

9: 99 percent / 30percent H₂O₂, LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

10: 1.) H₂, 2.) 6 N aq. HCl / 1.) 10percent Pd-C / 1.) glacial acetic acid/H₂O, 36 psi, 24 h

11: 1.) thioanisole, trifluoromethanesulfonic acid, 2.) Amberlite IR-120 (H+) resin / 1.) trifluoroacetic acid, -4 - 0 deg C, 30 min

With hydrogenchloride; lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; methyl-phenyl-thioether; 400 azide exchange resin; Amberlite IR-120 (H+) resin; Amberlite IR; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; hydrogen; dihydrogen peroxide; bromine; pivaloyl chloride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; acetonitrile;

DOI:10.1016/0040-4020(94)00996-8

Reference yield:

3,5-dimethylmethoxybenzene (874-63-5) → (2S,3R) 2-amino-3-(2',6'-dimethyl-4'-hydroxyphenyl)butanoic acid (143739-15-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / Br₂ / CCl₄ / -25 °C

2: 1.) Mg / 1.) THF, reflux, 4 h, 2.) THF, 0 deg C to RT; RT, 1 h

3: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

4: LiOH*H₂O / methanol; H₂O

5: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

6: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

7: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

8: 95 percent / Amberlite IR/400 azide exchange resin / acetonitrile / 216 h / Ambient temperature

9: 100 percent / 30percent H₂O₂, LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

10: 1.) H₂, 2.) 6 N aq. HCl / 1.) 10percent Pd-C / 1.) glacial acetic acid/H₂O, 36 psi, 24 h

11: 1.) thioanisole, trifluoromethanesulfonic acid, 2.) Amberlite IR-120 (H+) resin / 1.) trifluoroacetic acid, -4 - 0 deg C, 30 min

With hydrogenchloride; lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; methyl-phenyl-thioether; 400 azide exchange resin; Amberlite IR-120 (H+) resin; Amberlite IR; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; hydrogen; dihydrogen peroxide; bromine; pivaloyl chloride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; water; acetonitrile;

DOI:10.1016/0040-4020(94)00996-8

Reference yield:

2-bromo-5-methoxy-1,3-dimethyl-benzene (6267-34-1) → (2S,3R) 2-amino-3-(2',6'-dimethyl-4'-hydroxyphenyl)butanoic acid (143739-15-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Mg / 1.) THF, reflux, 4 h, 2.) THF, 0 deg C to RT; RT, 1 h

2: potassium tert-butoxide / tetrahydrofuran / 2 h / Ambient temperature

3: LiOH*H₂O / methanol; H₂O

4: 1.) pivaloyl chloride, triethylamine / 1.) THF, -78 deg C, 15 min then 0 deg C, 45 min, 2.) THF, -78 deg C, 20 min then RT, 2 h

5: CuBr*(CH₃)2S / tetrahydrofuran; various solvent(s); diethyl ether / -4 deg C, 90 min; RT, overnight

6: 1.) diisopropylethylamine, di-n-butylborontriflate, 2.) N-bromosuccinimide / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C, 2 h; -78 to -4 deg C

7: 95 percent / Amberlite IR/400 azide exchange resin / acetonitrile / 216 h / Ambient temperature

8: 100 percent / 30percent H₂O₂, LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

9: 1.) H₂, 2.) 6 N aq. HCl / 1.) 10percent Pd-C / 1.) glacial acetic acid/H₂O, 36 psi, 24 h

10: 1.) thioanisole, trifluoromethanesulfonic acid, 2.) Amberlite IR-120 (H+) resin / 1.) trifluoroacetic acid, -4 - 0 deg C, 30 min

With hydrogenchloride; lithium hydroxide; N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; methyl-phenyl-thioether; 400 azide exchange resin; Amberlite IR-120 (H+) resin; Amberlite IR; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; hydrogen; dihydrogen peroxide; pivaloyl chloride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; acetonitrile;

DOI:10.1016/0040-4020(94)00996-8

upstream raw materials:

3,5-dimethylmethoxybenzene

2-bromo-5-methoxy-1,3-dimethyl-benzene

4-methoxy-2,6-dimethylbenzylaldehyde

3(2S,3R),4(R) 3-<2-azido-3-(4'-methoxy-2',6'-dimethylphenyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone