(S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

Base Information

Chemical Name:(S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester
CAS No.:80185-83-7
Molecular Formula:C₂₆H₂₃ClN₂O₅
Molecular Weight:478.932
Hs Code.:

Synonyms:(S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

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Chemical Property of (S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

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Technology Process of (S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

There total 18 articles about (S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl 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: 65.0%

: 80132-10-1,80132-11-2
threo-DL-N-benzyloxycarbonyl-α-amino-3-oxo-5-isoxazolidineacetic acid diphenylmethyl ester

: 80148-34-1,80185-83-7,104832-75-9
threo-DL-N-benzyloxycarbonyl-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid diphenylmethyl ester

Guidance literature:: With hexamethylphosphorous triamide dichloride; triethylamine; In 1,4-dioxane; for 72h; Heating;
DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

: 80132-11-2
(S)-Benzyloxycarbonylamino-((R)-3-oxo-isoxazolidin-5-yl)-acetic acid benzhydryl ester

: 80185-83-7
(S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

Guidance literature:: With hexamethylphosphorous triamide dichloride; In tetrahydrofuran; Heating;
DOI:10.1021/ja00414a064

Reference yield:

: 56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
L-glutamic acid

: 80185-83-7
(S)-Benzyloxycarbonylamino-((R)-3-chloro-4,5-dihydro-isoxazol-5-yl)-acetic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Cl₂, H₂SO₄ / 5 h / Irradiation

2: 72 percent / pH 9

3: 82 percent / dicyclohexylcarbodiimide / ethyl acetate / 0 °C

4: tetrahydrofuran / -50 - -30 °C

5: hydroxylamine / H₂O / pH 6

6: Et₃N / H₂O / Ambient temperature; pH 11

7: tetrahydrofuran

8: dichlorotris(dimethylamino)phosphorane / tetrahydrofuran / Heating

With sulfuric acid; hexamethylphosphorous triamide dichloride; hydroxylamine; chlorine; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; ethyl acetate;
DOI:10.1021/ja00414a064