Benzylhydrazine dihydrochloride → HCID 66770916, compound

HRID 1697602Notes

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.Cl.C(NN)C1C=CC=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]([CH2:96][C:97]2[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=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:87])([F:88])[F:89])(=[O:78])=[O:79])[CH2:74][N:73]1[C:90]1[N:91]([CH2:96][C:97]2[CH:98]=[CH:99][CH:100]=[CH:101][CH:102]=2)[N:92]=[C:93]([CH3:95])[CH:94]=1)=[O:71]

Participants

Reactant 4

HCID 146540Benzylhydrazine dihydrochloride

HCID 66770698HCID 66770698, compound

HCID 86646823(2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HCID 86646844HCID 86646844, compound

Product 1

HCID 66770916HCID 66770916, 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 benzylhydrazine dihydrochloride (CAS Reg. No. 20570-96-1) to give a mixture of the title compound and (2R,4R)-1-(2-benzyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as orange oil. MS (ESI): m/z=508.2 [M+H]+.

Workup

customdescribed in example 192 h
custom20570-96-1) to give

Sources & evidence

ORD record: ord-aacd8e6e29a841a2a193918713ab14f8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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