(3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one

Base Information

• Chemical Name: (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one
• CAS No.: 179949-31-6
• Molecular Formula: C₂₇H₃₄N₂O₅
• Molecular Weight: 466.577

Synonyms:(3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one

Chemical Property of (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one

There total 6 articles about (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one 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: 80.0%

Methoxyacetyl chloride (38870-89-2) + (4S,5S)-4-[(E)-Benzylimino-methyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester → (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one (179949-31-6)

Guidance literature:

With triethylamine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/0040-4020(96)00463-2

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one (179949-31-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) Et₃N / 1.) toluene, reflux, 2.) CH₂Cl₂, 0 deg C, 4 h

2: 98 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 2 h / -15 - 0 °C

3: anhyd. MgSO₄ / CH₂Cl₂ / 24 h / Ambient temperature

4: 80 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

With oxalyl dichloride; magnesium sulfate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(96)00463-2

Reference yield:

(1S,2S)-2-amino-1-phenyl-1,3-diol (28143-91-1) → (3R,4S,4'S,5'S) N-benzyl-3-methoxy-4-(N-t-butoxycarbonyl-2',2'-dimethyl-5'-phenyl-1',3'-oxazolidin-4'-yl)azetidin-2-one (179949-31-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) Et₃N / 1.) toluene, reflux, 2.) CH₂Cl₂, 0 deg C, 4 h

2: 98 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 2 h / -15 - 0 °C

3: anhyd. MgSO₄ / CH₂Cl₂ / 24 h / Ambient temperature

4: 80 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

With oxalyl dichloride; magnesium sulfate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(96)00463-2

upstream raw materials:

Methoxyacetyl chloride

di-tert-butyl dicarbonate

(1S,2S)-2-amino-1-phenyl-1,3-diol

tert-butyl (4S,5S)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate

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