HCID 66883935, compound → HCID 59431065, compound

HRID 2204057Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14]/C=C/C)[C@@H:12]([O:18]/C=C/C)[C@H:11]([O:22]/C=C/C)[C@@H:10]([CH2:26][O:27]/C=C/C)[N:9]2[CH3:31])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[CH:35][CH:34]=1>C1COCC1.CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:18])[C@H:11]([OH:22])[C@@H:10]([CH2:26][OH:27])[N:9]2[CH3:31])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH3:41])=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Compound from Step B (54 mg, 0.093 mmol) was dissolved in a solution of THF/AcOH/1NHCl (0.5 ml:0.6 ml:0.30 ml) and heated to 70° C. for 30 minutes. The mixture was concentrated to give a pale yellow oil. Purification by preparative HPLC (sunfire C18, 30×100 mm, 5 μm, 10%-100% B over 15 minutes) afforded (2S,3S,4R,5R,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-1-methyl-piperidine-3,4,5-triol (22 mg, 0.052 mmol, 56%) as a white solid. MS (ES+) [M+H]+=422.

Workup

concentrationThe mixture was concentrated
customto give a pale yellow oil
customPurification by preparative HPLC (sunfire C18, 30×100 mm, 5 μm, 10%-100% B over 15 minutes)

Sources & evidence

ORD record: ord-6769b049364a4ff3a484bebef4c9efeb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365602B2

Reaction notes

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