1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline

Base Information

• Chemical Name: 1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline
• CAS No.: 64154-79-6
• Molecular Formula: C20H20N2O7
• Molecular Weight: 400.388
• DSSTox Substance ID: DTXSID50565038
• Nikkaji Number: J377.190C
• Wikidata: Q82449958
• Mol file: 64154-79-6.mol

Synonyms:64154-79-6;1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline;DTXSID50565038

Chemical Property of 1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 400.12705098
• Heavy Atom Count: 29
• Complexity: 602

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)C(=O)N2CCCC2C(=O)O)[N+](=O)[O-])OCC3=CC=CC=C3
• Isomeric SMILES: COC1=C(C=C(C(=C1)C(=O)N2CCC[C@H]2C(=O)O)[N+](=O)[O-])OCC3=CC=CC=C3

Technology Process of 1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline

There total 4 articles about 1-[4-(Benzyloxy)-5-methoxy-2-nitrobenzoyl]-L-proline 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:

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride (64154-78-5) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid (64154-79-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 22 ℃; 1) 0 deg C to RT, 2) RT, 30 min;

DOI:10.1016/S0040-4020(01)88134-5

Reference yield:

3-methoxy-4-hydroxybenzoic acid (121-34-6) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid (64154-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOH

2: HNO₃; H₂SO₄ / CH₂Cl₂ / -25 °C

3: SOCl₂ / benzene

4: TFA / tetrahydrofuran

With sodium hydroxide; thionyl chloride; sulfuric acid; nitric acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0960-894X(02)00326-8

Reference yield:

4-(benzyloxy)-3-methoxybenzoic acid (1486-53-9) → (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid (64154-79-6)

Guidance literature:

Multi-step reaction with 3 steps

1: HNO₃; H₂SO₄ / CH₂Cl₂ / -25 °C

2: SOCl₂ / benzene

3: TFA / tetrahydrofuran

With thionyl chloride; sulfuric acid; nitric acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1016/S0960-894X(02)00326-8

upstream raw materials:

4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

L-proline

3-methoxy-4-hydroxybenzoic acid

4-(benzyloxy)-3-methoxybenzoic acid

Downstream raw materials:

(11aS)-8-(benzyloxy)-1,2,3,10,11,11a-hexahydro-7-methoxy-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5,11-dione

(S)-methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylate

(2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl dithioacetal

(2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal