3-Methoxyphenylhydrazine hydrochloride → HCID 66770765, compound

HRID 1697606Notes

Reaction equation

HRID 1697606 reaction equation
COC([C@@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C(=S)CC(=O)C)=O.COC([C@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C(=S)CC(=O)C)=O.Cl.COC1C=C(NN)C=CC=1.[CH3:68][O:69][C:70]([C@H:72]1[CH2:76][C@@H:75]([S:77]([C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][C:81]=2[C:86]([F:89])([F:88])[F:87])(=[O:79])=[O:78])[CH2:74][N:73]1[C:90]1[N:91]([C:96]2[CH:101]=[CH:100][CH:99]=[C:98]([O:102][CH3:103])[CH:97]=2)[N:92]=[C:93]([CH3:95])[CH:94]=1)=[O:71]>>[CH3:68][O:69][C:70]([C@@H:72]1[CH2:76][C@@H:75]([S:77]([C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][C:81]=2[C:86]([F:89])([F:88])[F:87])(=[O:79])=[O:78])[CH2:74][N:73]1[C:90]1[N:91]([C:96]2[CH:101]=[CH:100][CH:99]=[C:98]([O:102][CH3:103])[CH:97]=2)[N:92]=[C:93]([CH3:95])[CH:94]=1)=[O:71]

Participants

5

Reactant 4

HCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 66770729HCID 66770729, compoundHCID 86646823(2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86646844HCID 86646844, compound

Product 1

HCID 66770765HCID 66770765, compound

Procedure

In analogy to the procedure described in example 192 h, a mixture of (2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192 g) and of (2R,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with 3-methoxyphenylhydrazin hydrochloride (CAS Reg. No. 39232-91-2) to give a mixture of the title compound and (2R,4R)-1-[2-(3-methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as orange oil. MS (ESI): m/z=524.3 [M+H]+.

Workup

  1. customdescribed in example 192 h
  2. custom39232-91-2) to give

Sources & evidence

ORD record
ord-a80adf56ce3e4b1f86e3b109b50eff43
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

Loading…