[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

Base Information

Chemical Name:[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester
CAS No.:329005-72-3
Molecular Formula:C₂₁H₃₀N₂O₇
Molecular Weight:422.478
Hs Code.:

Synonyms:[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

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Chemical Property of [(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

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Technology Process of [(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

There total 8 articles about [(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester 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: 89.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 329005-71-2
(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone

: 329005-72-3
[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

Guidance literature:: With hydrogen; 10percent Pd/C; In ethyl acetate; at 20 ℃; for 1.5h; under 760.051 Torr;
DOI:10.1021/jo001000k

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 329005-72-3
[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / DIEA / CH₂Cl₂ / 20 °C

2: 59 percent / TFA / CH₂Cl₂ / 0.13 h / 0 °C

3: 100 percent / NaH / tetrahydrofuran / 0 - 20 °C

4: 99 percent / Et₃N*3HF / tetrahydrofuran / 10 h / 50 °C

5: 86 percent / Et₃N / CH₂Cl₂ / 2.25 h / 0 °C

6: 98 percent / NaN₃ / dimethylformamide / 80 °C

7: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

With sodium azide; hydrogen; sodium hydride; triethylamine tris(hydrogen fluoride); triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001000k

Reference yield:

: 329005-69-8
(3S,5R)-3-benzyloxymethoxy-5-hydroxymethyl-N-[methoxycarbonylmethyl]-2-pyrrolidinone

: 329005-72-3
[(3S,5R)-3-Benzyloxymethoxy-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 2.25 h / 0 °C

2: 98 percent / NaN₃ / dimethylformamide / 80 °C

3: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

With sodium azide; hydrogen; triethylamine; 10percent Pd/C; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001000k