Phenelzine Sulfate → HCID 66770750, compound

HRID 1697610Notes

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.S(O)(O)(=O)=O.C(NN)CC1C=CC=CC=1.[CH3:72][O:73][C:74]([C@H:76]1[CH2:80][C@@H:79]([S:81]([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=2[C:90]([F:93])([F:92])[F:91])(=[O:83])=[O:82])[CH2:78][N:77]1[C:94]1[N:95]([CH2:100][CH2:101][C:102]2[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=2)[N:96]=[C:97]([CH3:99])[CH:98]=1)=[O:75]>>[CH3:72][O:73][C:74]([C@@H:76]1[CH2:80][C@@H:79]([S:81]([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=2[C:90]([F:91])([F:92])[F:93])(=[O:82])=[O:83])[CH2:78][N:77]1[C:94]1[N:95]([CH2:100][CH2:101][C:102]2[CH:103]=[CH:104][CH:105]=[CH:106][CH:107]=2)[N:96]=[C:97]([CH3:99])[CH:98]=1)=[O:75]

Participants

Reactant 4

HCID 61100Phenelzine Sulfate

HCID 66771188HCID 66771188, 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 66770750HCID 66770750, 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 2-phenethyl-hydrazine sulfate (CAS Reg. No. 56-51-4) to give a mixture of the title compound and (2R,4R)-1-(5-methyl-2-phenethyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as orange oil. MS (ESI): m/z=522.3 [M+H]+.

Workup

customdescribed in example 192 h
custom56-51-4) to give

Sources & evidence

ORD record: ord-685a3a16cf0b46f58b2c7b46a455a3ef
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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