(2S)-2-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-6-methylsulfonyl-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylic acid

Base Information

• Chemical Name: (2S)-2-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-6-methylsulfonyl-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylic acid
• CAS No.: 122620-17-1
• Molecular Formula: C₁₄H₁₆N₆O₇S₂
• Molecular Weight: 444.449
• Mol file: 122620-17-1.mol

Synonyms:LY 193239;LY-193239

Chemical Property of (2S)-2-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-6-methylsulfonyl-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylic acid

Chemical Property:

• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 444.05218922
• Heavy Atom Count: 29
• Complexity: 912

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CON=C(C1=CSC(=N1)N)C(=O)NC2CN3CC(=C(N3C2=O)C(=O)O)S(=O)(=O)C
• Isomeric SMILES: CO/N=C(\C1=CSC(=N1)N)/C(=O)NC2CN3CC(=C(N3C2=O)C(=O)O)S(=O)(=O)C

Technology Process of (2S)-2-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-6-methylsulfonyl-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylic acid

There total 6 articles about (2S)-2-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-6-methylsulfonyl-3-oxo-2,7-dihydro-1H-pyrazolo[1,2-a]pyrazole-5-carboxylic 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:

[2-((S)-4-tert-Butoxycarbonylamino-3-oxo-pyrazolidin-1-yl)-1-methanesulfonyl-ethyl]-phosphonic acid diethyl ester (140182-19-0) → 3-Methylsulfonyl-7-(S)-<2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylic acid (122620-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 23 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / -78 deg C to r.t.

3: 1.) Pd(OAc)2, PPh₃, 2.) Bu₃SnH

With palladium diacetate; tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane;

DOI:10.1016/S0040-4020(01)88183-7

Reference yield:

[2-((S)-4-tert-Butoxycarbonylamino-3-oxo-pyrazolidin-1-yl)-1-methanesulfonyl-ethyl]-phosphonic acid dimethyl ester (106892-80-2,122297-95-4,122332-42-7) → 3-Methylsulfonyl-7-(S)-<2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylic acid (122620-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1: iPr₂NEt / CH₂Cl₂ / -78 deg C to r.t.

2: iPr₂NEt

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/0040-4039(90)80153-D

Reference yield:

(S)-6-{2-(2-Allyloxycarbonylamino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-2-methanesulfonyl-7-oxo-6,7-dihydro-3H,5H-pyrazolo[1,2-a]pyrazole-1-carboxylic acid allyl ester (122548-62-3) → 3-Methylsulfonyl-7-(S)-<2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylic acid (122620-17-1)

Guidance literature:

With palladium diacetate; tri-n-butyl-tin hydride; triphenylphosphine; Yield given. Multistep reaction;

DOI:10.1016/S0040-4020(01)88183-7

upstream raw materials:

Allyl-<7-(S)-(tert-Butoxycarbonylamino)-3-methylsulfonyl>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylate

2-<2-<<(allyloxy)carbonyl>amino>thiazol-4-yl>-2-(Z)-(methoxyimino)acetic acid

(S)-6-{2-(2-Allyloxycarbonylamino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-2-methanesulfonyl-7-oxo-6,7-dihydro-3H,5H-pyrazolo[1,2-a]pyrazole-1-carboxylic acid allyl ester

[2-((S)-4-tert-Butoxycarbonylamino-3-oxo-pyrazolidin-1-yl)-1-methanesulfonyl-ethyl]-phosphonic acid diethyl ester