(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl ester

Base Information

• Chemical Name: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl ester
• CAS No.: 131244-03-6
• Molecular Formula: C₃₂H₃₈F₃N₃O₄
• Molecular Weight: 585.667

Synonyms:(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl ester

Chemical Property of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl ester

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Technology Process of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl ester

There total 13 articles about (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4,6,8⁽¹⁵⁾-tetraen-13-ylmethyl 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: 88.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (-)-pendolmycin (119375-01-8,138512-90-0) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-13-ylmethyl ester (131244-03-6)

Guidance literature:

With pyridine; at 20 ℃; for 1.75h;

DOI:10.1016/S0040-4020(01)87818-2

Reference yield:

N-Methyl-(S)-valin-tert-butylester (5616-87-5) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-13-ylmethyl ester (131244-03-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) ClCO₂Et-THF, Et₃N / 1) THF, -20 deg C, 15 min, 2a) -20 deg C, 15 min, 2b) 18 deg C, 1.5h

2: 31 mg / Mg / tetrahydrofuran / 2.25 h / -20 °C

3: 85 percent / p-TsOH*H₂O / benzene / 0.05 h / 90 °C

4: 78 percent / Lawesson reagent / tetrahydrofuran / 0.5 h / 80 °C

5: 73 percent / MeI / dimethylformamide / 18 h / 20 °C

6: 57 percent / Na₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

7: 90 percent / Al-Hg, water / tetrahydrofuran / 2 h / 45 - 50 °C

8: TFA / 28 h / 20 °C

9: 5percent Et₃N/DMF, 5percent DEPC/DMF / dimethylformamide / 24 h / 20 °C

10: 97 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 10 h / 20 °C

11: 88 percent / pyridine / 1.75 h / 20 °C

With Lawessons reagent; pyridine; sodium tetrahydroborate; aluminium amalgam; water; chloroformic acid ethyl ester; sodium carbonate; toluene-4-sulfonic acid; magnesium; triethylamine; N,N-dimethyl-formamide; diethyl dicarbonate; trifluoroacetic acid; lithium chloride; methyl iodide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)87818-2

Reference yield:

tert-Butyl L-N-<5,5-Dimethyl-4-(2-pyrrolyl)-3,6-heptadienoyl>-N-methylvalinate (131226-15-8) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (10S,13S)-5-(1,1-dimethyl-allyl)-10-isopropyl-9-methyl-11-oxo-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-13-ylmethyl ester (131244-03-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 78 percent / Lawesson reagent / tetrahydrofuran / 0.5 h / 80 °C

2: 73 percent / MeI / dimethylformamide / 18 h / 20 °C

3: 57 percent / Na₂CO₃ / CH₂Cl₂ / 18 h / 20 °C

4: 90 percent / Al-Hg, water / tetrahydrofuran / 2 h / 45 - 50 °C

5: TFA / 28 h / 20 °C

6: 5percent Et₃N/DMF, 5percent DEPC/DMF / dimethylformamide / 24 h / 20 °C

7: 97 percent / NaBH₄, LiCl / ethanol; tetrahydrofuran / 10 h / 20 °C

8: 88 percent / pyridine / 1.75 h / 20 °C

With Lawessons reagent; pyridine; sodium tetrahydroborate; aluminium amalgam; water; sodium carbonate; triethylamine; N,N-dimethyl-formamide; diethyl dicarbonate; trifluoroacetic acid; lithium chloride; methyl iodide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87818-2

upstream raw materials:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(-)-pendolmycin

N-Methyl-(S)-valin-tert-butylester

tert-Butyl L-N-Methyl-N-<7-(2-methyl-3-buten-2-yl)-4-indolyl>valinate

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