Hydrochloric Acid → 4-{4-[(1E)-4-(2,9-diazaspiro[5.5]undec-2-yl)but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside dihydrochloride

HRID 931673Notes

Reaction equation

HRID 931673 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5](/[CH:62]=[CH:63]/[CH2:64][CH2:65][N:66]2[CH2:71][CH2:70][CH2:69][C:68]3([CH2:76][CH2:75][N:74](C(OC(C)(C)C)=O)[CH2:73][CH2:72]3)[CH2:67]2)[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[C:11]([O:18][C@@H:19]2[O:51][C@H:50]([CH2:52][O:53][C:54](=[O:61])[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C@@H:40]([O:41][C:42](=[O:49])[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@H:30]([O:31][C:32](=[O:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:20]2[O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:12][NH:13][C:14]=1[CH:15]([CH3:17])[CH3:16]>ClCCl>[ClH:1].[ClH:1].[C:22]([O:21][C@@H:20]1[C@@H:30]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@H:40]([O:41][C:42](=[O:49])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:50]([CH2:52][O:53][C:54](=[O:61])[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[O:51][C@H:19]1[O:18][C:11]1[C:10]([CH2:9][C:8]2[CH:7]=[CH:6][C:5](/[CH:62]=[CH:63]/[CH2:64][CH2:65][N:66]3[CH2:71][CH2:70][CH2:69][C:68]4([CH2:72][CH2:73][NH:74][CH2:75][CH2:76]4)[CH2:67]3)=[CH:4][C:3]=2[CH3:2])=[C:14]([CH:15]([CH3:17])[CH3:16])[NH:13][N:12]=1)(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86720883tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 867208814-{4-[(1E)-4-(2,9-diazaspiro[5.5]undec-2-yl)but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside dihydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add hydrogen chloride (4.0 M solution in 1,4-dioxane, 0.6 mL, 2.4 mmol) to a solution of tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate (275 mg, 0.25 mmol) in dichloromethane (5 mL). After overnight (18 hours) at room temperature, concentrate to remove the solvent under reduced pressure to yield the title compound as a solid (258 mg, 0.24 mmol). MS (m/z): 1015.6 (M+1).

Workup

  1. concentrationconcentrate
  2. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-e2a091d284fe49d5a2d017097e8a80bb
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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