(3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl ester

Base Information

Chemical Name:(3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl ester
CAS No.:133230-47-4
Molecular Formula:C₂₇H₃₃N₃O₆
Molecular Weight:495.576
Hs Code.:
Mol file:133230-47-4.mol

Synonyms:(3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl ester

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Chemical Property of (3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl ester

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Technology Process of (3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl ester

There total 7 articles about (3S)-3-[(tert-Butoxycarbonyl)amino]-4-oxo-4-[[(S)-3-benzyl-2-oxopyrrolidin-3-yl]amino]butyric acid benzyl 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: 83.0%

: 7536-58-5,98482-77-0
BOC-L-aspartic acid 4-benzyl ester

: 133230-46-3
3-amino-3-benzylpyrrolidin-2-one

: 133230-47-4,133230-48-5
N-(Boc-Asp(OBn))-3-amino-3-benzyl-2-oxopyrrolidine

Guidance literature:: With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; from -15 deg C up to r.t., r.t. overnight;
DOI:10.1021/jo00012a022

Reference yield:

: 63-91-2,25191-15-5,658-69-5,67675-33-6
L-phenylalanine

: 133230-47-4,133230-48-5
N-(Boc-Asp(OBn))-3-amino-3-benzyl-2-oxopyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / triethylamine / dimethylformamide / 0 deg C and than r.t. overnight

2: 76 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / Heating; azeotropic removal of water

3: triethylamine, phosgene / acetonitrile; toluene / 2 h / 0 °C

4: concd. NH₄OH / tetrahydrofuran / Ambient temperature

5: 1.) N-methylmorpholine N-oxide, OsO₄, NaIO₄, 2.) trietylsilane, trifluoroacetic acid / 1.) acetonitrile, H₂O, toluene, r.t., 3 d, 2.) methylene dichloride, r.t., 18 h

6: saturated aqueous Ba(OH)2 / methanol / 18 h

7: 83 percent / N-methylmorpholine, isobutyl chloroformate / CH₂Cl₂ / from -15 deg C up to r.t., r.t. overnight

With 4-methyl-morpholine; triethylsilane; phosgene; barium dihydroxide; ammonium hydroxide; sodium periodate; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00012a022

Reference yield:

: 350-09-4
N-trifluoroacetyl-L-phenylalanine

: 133230-47-4,133230-48-5
N-(Boc-Asp(OBn))-3-amino-3-benzyl-2-oxopyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / Heating; azeotropic removal of water

2: triethylamine, phosgene / acetonitrile; toluene / 2 h / 0 °C

3: concd. NH₄OH / tetrahydrofuran / Ambient temperature

4: 1.) N-methylmorpholine N-oxide, OsO₄, NaIO₄, 2.) trietylsilane, trifluoroacetic acid / 1.) acetonitrile, H₂O, toluene, r.t., 3 d, 2.) methylene dichloride, r.t., 18 h

5: saturated aqueous Ba(OH)2 / methanol / 18 h

6: 83 percent / N-methylmorpholine, isobutyl chloroformate / CH₂Cl₂ / from -15 deg C up to r.t., r.t. overnight

With 4-methyl-morpholine; triethylsilane; phosgene; barium dihydroxide; ammonium hydroxide; sodium periodate; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00012a022