(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

Base Information

Chemical Name:(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate
CAS No.:690257-97-7
Molecular Formula:C₁₇H₂₂BrNO₄
Molecular Weight:384.27
Hs Code.:

Synonyms:(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

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Technology Process of (1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

There total 6 articles about (1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate 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: 86.0%

: 4530-20-5
BOC-glycine

: 690257-96-6
(2S,3E)-4-(4-bromophenyl)-3-buten-2-ol

: 690257-97-7
(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 5h;
DOI:10.1021/jm060015t

Reference yield:

: 20511-04-0,3815-31-4
(E)-4-(4-bromophenyl)but-3-ene-2-one

: 690257-97-7
(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

Guidance literature:: Multi-step reaction with 2 steps

1: 87.3 g / (R)-2-methyl-CBS-oxazaborolidine; catecholborane / toluene / 17 h / -78 °C

2: 86 percent / EDC; HOBt; N,N'-diisopropylethylamine / CH₂Cl₂ / 5 h

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;
DOI:10.1021/jm060015t

Reference yield:

: 1200-07-3,5676-63-1,17916-60-8
trans-4-bromocinnamic acid

: 690257-97-7
(1S,2E)-3-(4-bromophenyl)-1-methylprop-2-en-1-yl N-(tert-butoxycarbonyl)glycinate

Guidance literature:: Multi-step reaction with 3 steps

1.1: N,O-dimethylhydroxylamine*hydrochloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

1.2: 1 h / -78 - 0 °C

2.1: (R)-2-methyl-CBS-oxazaborolidine / toluene / 0.25 h / 20 °C

2.2: 5.5 - 25.5 h / -78 °C

3.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h

With N,O-dimethylhydroxylamine*hydrochloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; (R)-2-methyl-CBS-oxazaborolidine; In dichloromethane; toluene;