Trifluoroacetic acid → HCID 18727202, compound

HRID 1856898Notes

Reaction equation

FC(F)(F)C(O)=O.C([O:12][NH:13][C:14]([C@H:16]1[CH2:21][N:20]([C:22]([NH:24]C(C)(C)C)=[O:23])[CH2:19][CH2:18][N:17]1[S:29]([N:32]1[CH2:37][CH2:36][CH:35]([C:38](=[O:46])[C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[CH2:34][CH2:33]1)(=[O:31])=[O:30])=[O:15])(C)(C)C>>[OH:12][NH:13][C:14]([C@H:16]1[CH2:21][N:20]([C:22]([NH2:24])=[O:23])[CH2:19][CH2:18][N:17]1[S:29]([N:32]1[CH2:37][CH2:36][CH:35]([C:38](=[O:46])[C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)[CH2:34][CH2:33]1)(=[O:30])=[O:31])=[O:15]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 18727277HCID 18727277, compound

Product 1

HCID 18727202HCID 18727202, compoundYield 55%

Procedure

Trifluoroacetic acid (15 ml) was added to N-tert-butoxy-4-tert-butylaminocarbonyl-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (0.45 g, 0.92 mmol) [prepared as described in Step 2 above] and the reaction was stirred for 36 h. The reaction was concentrated in vacuo, and the residue was chromatographed (SiO2, PTLC, 10% methanol/methylene chloride) to give N-hydroxy-1-[4-(4-chlorobenzoyl)piperidine-1-sulfonyl]-4-aminocarbonylpiperazine-2-(R)-carboxamide (55%) as a pale pink solid.

Workup

concentrationThe reaction was concentrated in vacuo
customthe residue was chromatographed (SiO2, PTLC, 10% methanol/methylene chloride)

Sources & evidence

ORD record: ord-9cad1790b79f49e89ee6a06061159e5d
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143744

Reaction notes

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