(2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 1054625-30-7
• Molecular Formula: C₁₉H₂₈N₂O₇S₂
• Molecular Weight: 460.573

Synonyms:(2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester

There total 8 articles about (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic 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:

1-tert-butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate (254881-77-1,1018667-18-9) → (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester (1054625-30-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 18 h

2: 76 percent / DBU / dimethylformamide / 18 h

3: TFA / CH₂Cl₂ / 2 h

4: Et₃N / dioxane; H₂O / 16 h

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

Reference yield:

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (114676-69-6) → (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester (1054625-30-7)

Guidance literature:

Multi-step reaction with 7 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: 59 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

3: 61 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

4: 98 percent / Et₃N / CH₂Cl₂ / 18 h

5: 76 percent / DBU / dimethylformamide / 18 h

6: TFA / CH₂Cl₂ / 2 h

7: Et₃N / dioxane; H₂O / 16 h

With formic acid; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm000246e

Reference yield:

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride (114676-59-4) → (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester (1054625-30-7)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N; DMAP / H₂O; acetone / 16 h

2: Et₃N / CH₂Cl₂ / 20 °C

3: 59 percent / NaN₃ / dimethylformamide / 26 h / 55 °C

4: 61 percent / H₂; HCOOH / 10percent Pd/C / ethanol; tetrahydrofuran / 16 h / 2792.67 Torr

5: 98 percent / Et₃N / CH₂Cl₂ / 18 h

6: 76 percent / DBU / dimethylformamide / 18 h

7: TFA / CH₂Cl₂ / 2 h

8: Et₃N / dioxane; H₂O / 16 h

With dmap; formic acid; sodium azide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm000246e

upstream raw materials:

4-butoxybenzene-sulfonyl chloride

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

1-tert-butyl 2-methyl (2R,4S)-4-aminopyrrolidine-1,2-dicarboxylate

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