2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid

Base Information

• Chemical Name: 2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid
• CAS No.: 210288-67-8
• Molecular Formula: C₁₂H₁₃IN₂O₃
• Molecular Weight: 360.151
• DSSTox Substance ID: DTXSID70471541
• Wikidata: Q76421966
• Mol file: 210288-67-8.mol

Synonyms:210288-67-8;2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid;SCHEMBL8503323;DTXSID70471541

Chemical Property of 2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid

Chemical Property:

• PSA: 69.64000
• LogP: 1.59430
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 359.99709
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC2=C(C=CC(=C2)I)NC(C1=O)CC(=O)O
• Isomeric SMILES: CN1CC2=C(C=CC(=C2)I)N[C@H](C1=O)CC(=O)O

Technology Process of 2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid

There total 10 articles about 2-[(2S)-7-iodo-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid 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:

(2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid sodium salt → (2S)-2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid (210288-67-8)

Guidance literature:

With pyridine iodine monochloride; sodium hydroxide; In water; at 0 - 10 ℃; for 1h; pH=6.5 - 7.5; Industrial scale;

DOI:10.1021/op034023k

Reference yield:

(2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid (210288-68-9) → (2S)-2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid (210288-67-8)

Guidance literature:

With sodium hydroxide; C₅H₅N*ClH*I₂; In water; at 10 ℃; pH=7.0;

DOI:10.1016/S0040-4039(01)00843-7

Reference yield:

2-Nitrobenzyl alcohol (612-25-9) → (2S)-2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid (210288-67-8)

Guidance literature:

Multi-step reaction with 9 steps

1: NEt₃ / tetrahydrofuran / 20 °C

2: H₂O / 20 °C

3: 100 percent / toluene / 20 °C

4: H₂ / Raney-Ni / methanol / 50 °C / 2585.74 Torr

5: AcOH / 65 °C

6: NaOMe / methanol / 65 °C

7: 93 percent / H₂ / Pd/C / methanol / 60 °C / 3102.89 Torr

8: Candida antarctica lipase B; t-BuOH; NH₃ / H₂O / 50 °C / pH 7.0

9: pyridine iodine monochloride complex; NaOH / H₂O / 10 °C / pH 7.0

With Candida antarctica lipase B; sodium hydroxide; C₅H₅N*ClH*I₂; ammonia; hydrogen; sodium methylate; acetic acid; triethylamine; tert-butyl alcohol; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1016/S0040-4039(01)00843-7

upstream raw materials:

(2S)-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic acid

2-Nitrobenzyl alcohol

(2-nitrobenzyl)methylamine

methyl 2-(2-methoxy-2-oxoethyl)-3-methyl-1,2,3,4-tetrahydroquinazoline-2-carboxylate

Downstream raw materials:

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