Piperidine → HCID 178423761, compound

HRID 2167015Notes

Reaction equation

C([O:5][NH:6][C:7](=[N:59]S(C1C(C)=C(C)C2OC(C)(C)CC=2C=1C)(=O)=O)[NH:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:41]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[C:13](=[O:40])[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)=[CH:27][C:26]([C:36]([F:39])([F:38])[F:37])=[N:25]2)=[CH:20][CH:19]=1)(=[O:17])=[O:16])(C)(C)C.N1CCCCC1>CN(C)C=O>[NH2:41][C@@H:12]([CH2:11][CH2:10][CH2:9][NH:8][C:7]([NH2:59])=[N:6][OH:5])[C:13]([NH:14][S:15]([C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:28]([C:29]3[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=3)=[CH:27][C:26]([C:36]([F:39])([F:38])[F:37])=[N:25]2)=[CH:22][CH:23]=1)(=[O:16])=[O:17])=[O:40]

Participants

Conditions

Temperature: 25 °C

Procedure

Compound (15a) is treated with 20-50% piperidine in N,N-dimethylformamide (0.1 M) to remove the Fmoc protecting group. The residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid) and then dissolved in 95% trifluoroacetic acid-methylene chloride (0.1 M). The mixture is stirred at 25° C. for 6 h and then concentrated under reduced pressure. The residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid) to provide the title compound.

Workup

customto remove the Fmoc protecting group
customThe residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid)
dissolutiondissolved in 95% trifluoroacetic acid-methylene chloride (0.1 M)
concentrationconcentrated under reduced pressure
customThe residue is purified by reverse phase chromatography (acetonitrile/water with 0.05% trifluoroacetic acid)

Sources & evidence

ORD record: ord-a18da48203c34bd39d301fa12ad72b25
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09044464B2

Reaction notes

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