(2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid

Base Information

• Chemical Name: (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid
• CAS No.: 115288-84-1
• Molecular Formula: C₂HF₃O₂*C₂₄H₂₉BrN₂O₆
• Molecular Weight: 635.432

Synonyms:(2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid

Chemical Property of (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid

There total 17 articles about (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid 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:

meta-hydroxybenzaldehyde (100-83-4) → (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid (115288-84-1)

Guidance literature:

Multi-step reaction with 15 steps

1: i-Pr₂NEt / 1,2-dichloro-ethane / 70 °C

2: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -78 °C

3: NH₃ / methanol / Ambient temperature

4: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / -20 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

6: HgCl₂, CSA / acetonitrile; H₂O / 0.33 h / 40 °C

7: 59 percent / NaBH₄ / methanol; CH₂Cl₂ / 0 °C

8: H₂ / Ra-Ni (W₂) / ethanol / 1.5 h / 100 °C / 103430 Torr

9: NaHCO₃ / ethanol / Ambient temperature

10: 78 percent / Br₂ / CH₂Cl₂ / Ambient temperature

11: 100 percent / pyridine / 0.17 h / 60 °C

12: 92 percent / DMAP, Et₃N / 1,2-dichloro-ethane / 0.5 h / 80 °C

13: 97 percent / NaBH₄ / methanol / 0 °C

14: 97 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

15: Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; Ra-Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00223a052

Reference yield:

3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzaldehyde (115288-69-2) → (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid (115288-84-1)

Guidance literature:

Multi-step reaction with 14 steps

1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -78 °C

2: NH₃ / methanol / Ambient temperature

3: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / -20 °C

4: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

5: HgCl₂, CSA / acetonitrile; H₂O / 0.33 h / 40 °C

6: 59 percent / NaBH₄ / methanol; CH₂Cl₂ / 0 °C

7: H₂ / Ra-Ni (W₂) / ethanol / 1.5 h / 100 °C / 103430 Torr

8: NaHCO₃ / ethanol / Ambient temperature

9: 78 percent / Br₂ / CH₂Cl₂ / Ambient temperature

10: 100 percent / pyridine / 0.17 h / 60 °C

11: 92 percent / DMAP, Et₃N / 1,2-dichloro-ethane / 0.5 h / 80 °C

12: 97 percent / NaBH₄ / methanol / 0 °C

13: 97 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

14: Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; mercury dichloride; Ra-Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00223a052

Reference yield:

1,4-Diacetyl-3-prop-2-ynyl-piperazine-2,5-dione → (2S,3S,5R)-3-Acetoxymethyl-2-[(R)-1-amino-2-(2-bromo-5-hydroxy-phenyl)-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester; compound with trifluoro-acetic acid (115288-84-1)

Guidance literature:

Multi-step reaction with 15 steps

1: AIBN / benzene

2: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / -78 °C

3: NH₃ / methanol / Ambient temperature

4: 82 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / -20 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -20 °C

6: HgCl₂, CSA / acetonitrile; H₂O / 0.33 h / 40 °C

7: 59 percent / NaBH₄ / methanol; CH₂Cl₂ / 0 °C

8: H₂ / Ra-Ni (W₂) / ethanol / 1.5 h / 100 °C / 103430 Torr

9: NaHCO₃ / ethanol / Ambient temperature

10: 78 percent / Br₂ / CH₂Cl₂ / Ambient temperature

11: 100 percent / pyridine / 0.17 h / 60 °C

12: 92 percent / DMAP, Et₃N / 1,2-dichloro-ethane / 0.5 h / 80 °C

13: 97 percent / NaBH₄ / methanol / 0 °C

14: 97 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

15: Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; bromine; sodium hydrogencarbonate; triethylamine; mercury dichloride; Ra-Ni (W₂); In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1021/ja00223a052

upstream raw materials:

(2R,3R,5S)-3-Acetoxymethyl-2-[(S)-2-(2-bromo-5-hydroxy-phenyl)-1-tert-butoxycarbonylamino-ethyl]-5-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

trifluoroacetic acid

meta-hydroxybenzaldehyde

3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-benzaldehyde

Downstream raw materials:

(1R,3R)-3-((2S,3S,5R)-3-Acetoxymethyl-1-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidin-2-yl)-5-bromo-8-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid tert-butyl ester

(1S,3R)-3-((2S,3S,5R)-3-Acetoxymethyl-1-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidin-2-yl)-5-bromo-8-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid tert-butyl ester

C₃₃H₃₆BrN₃O₈

(1R,3R)-8-Acetoxy-3-((2S,3S,5R)-3-acetoxymethyl-1-benzyloxycarbonyl-5-hydroxymethyl-pyrrolidin-2-yl)-5-bromo-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid tert-butyl ester

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