methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate

Base Information

• Chemical Name: methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate
• CAS No.: 251455-75-1
• Molecular Formula: C₁₈H₂₃N₃O₅
• Molecular Weight: 361.398

Synonyms:methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate

Chemical Property of methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate

Chemical Property:

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Technology Process of methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate

There total 2 articles about methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate 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: 31.0%

1-(methoxycarbonylacetyl)-2-[(S)-2-(tert-butyloxycarbonylamino)-3-phenylpropanoyl]hydrazine (251455-73-9) → methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate (251455-75-1)

Guidance literature:

1-(methoxycarbonylacetyl)-2-[(S)-2-(tert-butyloxycarbonylamino)-3-phenylpropanoyl]hydrazine; With pyridine; thionyl chloride; In tetrahydrofuran; at 0 ℃; for 2h;

In toluene; for 1.5h; Heating;

DOI:10.1021/jm990197+

Reference yield:

(S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate (30189-48-1) → methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate (251455-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 58 percent / N-methylmorpholine / tetrahydrofuran / -30 - 20 °C

2.1: SOCl₂; pyridine / tetrahydrofuran / 2 h / 0 °C

2.2: 31 percent / toluene / 1.5 h / Heating

With 4-methyl-morpholine; pyridine; thionyl chloride; In tetrahydrofuran; 1.1: Acylation / 2.1: Cyclization / 2.2: Dehydration;

DOI:10.1021/jm990197+

Reference yield:

methyl 2-{5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,3,4-oxadiazol-2-yl}acetate (251455-75-1) → [5-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-[1,3,4]oxadiazol-2-yl]-acetic acid (251455-92-2)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 3h;

DOI:10.1021/jm990197+

upstream raw materials:

1-(methoxycarbonylacetyl)-2-[(S)-2-(tert-butyloxycarbonylamino)-3-phenylpropanoyl]hydrazine

(S)-tert-butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate

Downstream raw materials:

[5-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-[1,3,4]oxadiazol-2-yl]-acetic acid

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