(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

Base Information

Chemical Name:(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester
CAS No.:338386-42-8
Molecular Formula:C₂₉H₃₆N₂O₆
Molecular Weight:508.615
Hs Code.:

Synonyms:(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

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Chemical Property of (S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

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Technology Process of (S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

There total 9 articles about (S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic 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: 86.0%

: 338386-48-4
(S)-(1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-yl)-methyl-carbamic acid benzyl ester

: 5437-45-6
Benzyl bromoacetate

: 338386-42-8
(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

Guidance literature:: With potassium carbonate; In acetonitrile; at 35 - 40 ℃; for 15h;
DOI:10.1021/ol015626o

Reference yield:

: 113089-15-9
(S)-2-methoxycarbonylamino-3-(4-methoxyphenyl)-propionic acid methyl ester

: 338386-42-8
(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / NaOH; H₂O / dioxane / 0.5 h / 0 °C

2.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 1-hydroxybenzotriazole hydrate; N-methyl morpholine / dimethylformamide; CH₂Cl₂ / 24 h / 20 °C

3.1: bis(trifluoroacetoxy)iodobenzene; MeOH / CH₂Cl₂; methanol / 0.17 h / 0 °C

3.2: 69 percent / H₂O / 0.08 h / 0 °C

4.1: 96 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C / 760.05 Torr

5.1: 90 percent / pyridinium p-toluenesulfonate / benzene / 3.5 h / Heating

6.1: 65 percent / LiAlH₄ / tetrahydrofuran / 11 h / Heating

7.1: 91 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

8.1: 84 percent / Zn; AcOH / 5 h / 75 °C

9.1: 86 percent / K₂CO₃ / acetonitrile / 15 h / 35 - 40 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; lithium aluminium tetrahydride; water; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol015626o

Reference yield:

: 338386-37-1
(S)-(1-methoxy-2,8-dioxo-1-azaspiro[4.5]deca-6,9-dien-3-yl)-carbamic acid methyl ester

: 338386-42-8
(S)-[11-(benzyloxycarbonyl-methyl-amino)-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-9-yl]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / H₂ / Pd/C / ethyl acetate / 6 h / 20 °C / 760.05 Torr

2: 90 percent / pyridinium p-toluenesulfonate / benzene / 3.5 h / Heating

3: 65 percent / LiAlH₄ / tetrahydrofuran / 11 h / Heating

4: 91 percent / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

5: 84 percent / Zn; AcOH / 5 h / 75 °C

6: 86 percent / K₂CO₃ / acetonitrile / 15 h / 35 - 40 °C

With lithium aluminium tetrahydride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; triethylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile; benzene;
DOI:10.1021/ol015626o