Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

Base Information

• Chemical Name: Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate
• CAS No.: 394735-24-1
• Molecular Formula: C₂₂H₃₆N₂O₅
• Molecular Weight: 408.538
• Mol file: 394735-24-1.mol

Synonyms:SCHEMBL16300708;DTXSID601101421;394735-24-1;Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

Chemical Property of Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 408.26242225
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2C1C(N(C2)C(=O)C(C3CCCCC3)NC(=O)OC(C)(C)C)C(=O)OC)C
• Isomeric SMILES: CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C3CCCCC3)NC(=O)OC(C)(C)C)C(=O)OC)C

Technology Process of Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate

There total 9 articles about Methyl (1R,2S,5S)-3-[(2S)-2-cyclohexyl-2-[[(1,1-dimethylethoxy)carbonyl]amino]acetyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate 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:

methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride + N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-24-1)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/jm060325b

Reference yield:

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one (134107-65-6) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-24-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BuLi / tetrahydrofuran

1.2: tetrahydrofuran / -78 - 20 °C

2.1: LiAlH₄ / tetrahydrofuran / Heating

3.1: H₂ / Pd/C

4.1: acetone / 3 h / -5 °C

5.1: toluene; methanol

6.1: HCl / dioxane

7.1: 6.0 g / BOP / CH₂Cl₂ / 15 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetone; toluene; 4.1: Jones oxidation;

DOI:10.1021/jm060325b

Reference yield:

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one (103201-79-2,1820583-17-2) → (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester (394735-24-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KHMDS; PhSeCl / -78 - 20 °C

1.2: H₂O₂; pyridine

2.1: BuLi / tetrahydrofuran

2.2: tetrahydrofuran / -78 - 20 °C

3.1: LiAlH₄ / tetrahydrofuran / Heating

4.1: H₂ / Pd/C

5.1: acetone / 3 h / -5 °C

6.1: toluene; methanol

7.1: HCl / dioxane

8.1: 6.0 g / BOP / CH₂Cl₂ / 15 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; Phenylselenyl chloride; hydrogen; potassium hexamethylsilazane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetone; toluene; 5.1: Jones oxidation;

DOI:10.1021/jm060325b

upstream raw materials:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate

(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

Downstream raw materials:

C₁₇H₂₈N₂O₃