(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

Base Information

• Chemical Name: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester
• CAS No.: 167937-54-4
• Molecular Formula: C₃₇H₃₇F₃N₂O₅
• Molecular Weight: 646.706

Synonyms:(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

Chemical Property of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

There total 11 articles about (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl 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: 77.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + N-[(3R,4R)-hexahydro-4-hydroxy-1-(phenylmethyl)-1H-azepin-3-yl]-4-(phenylmethoxy)benzamide (167937-56-6) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester (167937-54-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1021/np0705357

Reference yield:

caprolactam (105-60-2,9012-16-2) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester (167937-54-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / NaH / paraffin; tetrahydrofuran / 1.) 0 deg C to room temperature, 2 h, 2.) room temperature, 2 h

2: 80 percent / LiHMDS / tetrahydrofuran / 1.) -45 deg C to 0 deg C, 30 min, 2.) -45 deg C to room temperature, 5 h

3: 98 percent / H₂O₂ / CH₂Cl₂; pyridine / Heating

4: 78 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 36 h

5: 1.) BF₃*Et₂O, 2.) DBU / 1.) CH₂Cl₂, room temperature, 2 h, 2.) Ch₂Cl₂,

6: 1.) 2,6-lutidine, triflic anhydride, 2.) NaN₃, benzyltrimethylammonium bromide / 1.) CH₂Cl₂, 0 deg C, 16 h, 2.) CH₃OH, DMF, 3 d

7: LiAlH₄ / tetrahydrofuran / 1 h / Heating

8: 1N NaOH, Na₂CO₃, H₂O / CH₂Cl₂ / 16 h

9: 490 mg / DMAP, NEt₃ / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; dihydrogen peroxide; trimethylbenzylammonium bromide; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; acetone; paraffin; tert-butyl alcohol;

DOI:10.1021/jo952280k

Reference yield:

1-Benzyl-hexahydro-azepin-2-on (33241-96-2) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-1-benzyl-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester (167937-54-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / LiHMDS / tetrahydrofuran / 1.) -45 deg C to 0 deg C, 30 min, 2.) -45 deg C to room temperature, 5 h

2: 98 percent / H₂O₂ / CH₂Cl₂; pyridine / Heating

3: 78 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O; 2-methyl-propan-2-ol / 36 h

4: 1.) BF₃*Et₂O, 2.) DBU / 1.) CH₂Cl₂, room temperature, 2 h, 2.) Ch₂Cl₂,

5: 1.) 2,6-lutidine, triflic anhydride, 2.) NaN₃, benzyltrimethylammonium bromide / 1.) CH₂Cl₂, 0 deg C, 16 h, 2.) CH₃OH, DMF, 3 d

6: LiAlH₄ / tetrahydrofuran / 1 h / Heating

7: 1N NaOH, Na₂CO₃, H₂O / CH₂Cl₂ / 16 h

8: 490 mg / DMAP, NEt₃ / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; dihydrogen peroxide; trimethylbenzylammonium bromide; sodium carbonate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo952280k

upstream raw materials:

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

caprolactam

1-Benzyl-hexahydro-azepin-2-on

benzyl bromide

Downstream raw materials:

N-[(3R,4R)-hexahydro-4-hydroxy-1-(phenylmethyl)-1H-azepin-3-yl]-4-(phenylmethoxy)benzamide

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