Dimethylformamide dimethyl acetal → HCID 178484363, compound

HRID 515644Notes

Reaction equation

[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35](=[S:37])[NH2:36])[CH2:24][CH2:23]1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:40](OC)[N:41]([CH3:43])[CH3:42]>O1CCOCC1>[CH2:1]([O:8][N:9]([C@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[C@H:25]([C:35](=[S:37])/[N:36]=[CH:40]/[N:41]([CH3:43])[CH3:42])[CH2:24][CH2:23]1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:11])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamothioylpiperidine-1-carboxylate (1.65 g, 3 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (1.08 g, 9.0 mmol) in dry dioxane (20 mL) was stirred at 45° C. overnight. The reaction mixture was concentrated under vacuum and the residue was purified by silica gel column chromatography (1:1 petroleum ether/EtOAc) to give (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-((E)-(dimethylamino)methylenecarbamothioyl)piperidine-1-carboxylate (1.3 g, 72%) as a yellow solid. ESI-MS (EI+, m/z): 606 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated under vacuum
customthe residue was purified by silica gel column chromatography (1:1 petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-e6fe7fad13674f13a8a2644901eec901
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108966B2

Reaction notes

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