2,2,2-Trifluoroethyl trichloromethanesulphonate → HCID 10321784, compound

HRID 843031Notes

Reaction equation

HRID 843031 reaction equation
C(O[C:9]([N:11]1CCN(CC(F)(F)F)C[CH:12]1C(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.ClC(Cl)(Cl)S(OCC(F)(F)F)(=O)=[O:35].[OH:45][NH:46][C:47]([CH:49]1[CH2:54][N:53]([CH2:55]C(F)(F)F)[CH2:52][CH2:51][N:50]1[S:60]([N:63]1[CH2:68][CH:67]=[C:66]([C:69]2[CH:74]=[CH:73][C:72]([F:75])=[CH:71][CH:70]=2)[CH2:65][CH2:64]1)(=[O:62])=[O:61])=[O:48]>>[OH:45][NH:46][C:47]([C@H:49]1[CH2:54][N:53]([C:55]([N:11]([CH3:12])[CH3:9])=[O:35])[CH2:52][CH2:51][N:50]1[S:60]([N:63]1[CH2:68][CH:67]=[C:66]([C:69]2[CH:70]=[CH:71][C:72]([F:75])=[CH:73][CH:74]=2)[CH2:65][CH2:64]1)(=[O:61])=[O:62])=[O:48]

Participants

4

Reactant 3

HCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 22615545HCID 22615545, compoundHCID 22615719HCID 22615719, compound

Product 1

HCID 10321784HCID 10321784, compound

Procedure

Proceeding as described in Example 28, Step 1 above, but substituting 1-benzyloxycarbonyl-4-tert-butoxycarbonylpiperazine-2-(R)-carboxylic acid with benzyl 1-benzyioxycarbonyl-4-tert-butoxycarbonylpiperazine-2-(RS)-carboxylate [prepared from 1-benzyloxycarbonyl-4-tert-butoxycarbonylpiperazine-2-(RS)-carboxylic acid as described in Ono, N., et al. Bull. Chem. Soc. Jpn., 51, 2401, (1978)] gave benzyl 1-benzyloxycarbonylpiperazine-2-(RS)-carboxylatc. This material was first converted to benzyl 1-benzyloxycarbonyl-4-(2,2,2-trifluoroethyl)piperazine-2-(RS)-carboxylate by reacting it with 2,2,2-trifluoroethyl trichloromethanesulfonate as described in Gao, Y., et al. J. Med. Chem., 33, 39, (1990) and then to N-hydroxy-1-[4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine-1-sulfonyl]-4-(2,2,2-trifluoroethyl)piperazine-2-(RS)-carboxamide by following Example 28, Steps 3-5 described above.

Sources & evidence

ORD record
ord-d411776ab66742ca81ac1476a47b7c81
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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