Diisopropylethylamine → tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1 h-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,6-diazaspiro[3.5]nonane-6-carboxylate

HRID 2366518Notes

Reaction equation

C(N(C(C)C)CC)(C)C.CS(O[CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]2[C:27]([O:34][C@@H:35]3[O:52][C@H:51]([CH2:53][O:54][C:55](=[O:57])[CH3:56])[C@@H:46]([O:47][C:48](=[O:50])[CH3:49])[C@H:41]([O:42][C:43](=[O:45])[CH3:44])[C@H:36]3[O:37][C:38](=[O:40])[CH3:39])=[N:28][NH:29][C:30]=2[CH:31]([CH3:33])[CH3:32])=[C:21]([CH3:58])[CH:20]=1)(=O)=O.[CH2:59]1[C:62]2([CH2:67][CH2:66][CH2:65][N:64]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:63]2)[CH2:61][NH:60]1>C(#N)C>[CH3:58][C:21]1[CH:20]=[C:19](/[CH:18]=[CH:17]/[CH2:16][CH2:15][N:60]2[CH2:61][C:62]3([CH2:67][CH2:66][CH2:65][N:64]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:63]3)[CH2:59]2)[CH:24]=[CH:23][C:22]=1[CH2:25][C:26]1[C:27]([O:34][C@@H:35]2[O:52][C@H:51]([CH2:53][O:54][C:55](=[O:57])[CH3:56])[C@@H:46]([O:47][C:48](=[O:50])[CH3:49])[C@H:41]([O:42][C:43](=[O:45])[CH3:44])[C@H:36]2[O:37][C:38](=[O:40])[CH3:39])=[N:28][NH:29][C:30]=1[CH:31]([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 80 °C

Procedure

Add diisopropylethylamine (0.2 mL, 1.1 mmol) to a solution of (3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate (200 mg, 0.28 mmol) and tert-butyl 2,6-diazaspiro[3.5]nonane-6-carboxylate (77 mg, 0.34 mmol) in acetonitrile (3 mL). Heat the mixture at 80° C. for overnight. Concentrate under reduced pressure and purify residue by flash chromatography to yield the title compound (127 mg, 0.15 mmol). MS (m/z): 838.8, 839.6 (M+1), 836.8, 837.6 (M−1).

Workup

concentrationConcentrate under reduced pressure
custompurify residue by flash chromatography

Sources & evidence

ORD record: ord-6b08bcd0ce1842f093ee7c205035694c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697849B2

Reaction notes

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