Lawesson's reagent → HCID 67278578, compound

HRID 1697706Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24](=O)[CH2:25][C:26](=O)[CH3:27])=[O:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.Cl.[CH:53]1([NH:57][NH2:58])[CH2:56][CH2:55][CH2:54]1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[C:20]([F:22])([F:23])[F:21])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24]1[N:57]([CH:53]2[CH2:56][CH2:55][CH2:54]2)[N:58]=[C:26]([CH3:27])[CH:25]=1)=[O:4]

Participants

Reactant 3

HCID 87949Lawesson's reagent

HCID 19432792Cyclobutylhydrazine--hydrogen chloride (1/1)

HCID 86646861HCID 86646861, compound

Product 1

HCID 67278578HCID 67278578, compound

Procedure

In analogy to the procedure described in example 308d, (2S,4R)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) and cyclobutylhydrazine hydrochloride (CAS Reg. No. 158001-21-9) to give the title compound as brown oil. MS (ESI): m/z=549.8 [M+H]+.

Sources & evidence

ORD record: ord-78667ddc80f44f79aea6e9fe57d7e4fa
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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