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-acetyl-beta-D-glucopyranoside dihydrochloride

HRID 931677Notes

Reaction equation

HRID 931677 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5](/[CH:42]=[CH:43]/[CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][CH2:49][C:48]3([CH2:56][CH2:55][N:54](C(OC(C)(C)C)=O)[CH2:53][CH2:52]3)[CH2:47]2)[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[C:11]([O:18][C@@H:19]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:41])[CH3:40])[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]2[O:21][C:22](=[O:24])[CH3:23])=[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:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@@H:35]([CH2:37][O:38][C:39](=[O:41])[CH3:40])[O:36][C@H:19]1[O:18][C:11]1[C:10]([CH2:9][C:8]2[CH:7]=[CH:6][C:5](/[CH:42]=[CH:43]/[CH2:44][CH2:45][N:46]3[CH2:51][CH2:50][CH2:49][C:48]4([CH2:52][CH2:53][NH:54][CH2:55][CH2:56]4)[CH2:47]3)=[CH:4][C:3]=2[CH3:2])=[C:14]([CH:15]([CH3:17])[CH3:16])[NH:13][N:12]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86715154tert-butyl 2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosy)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 867208844-{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-acetyl-beta-D-glucopyranoside dihydrochlorideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add hydrogen chloride (4.0 M solution in 1,4-dioxane, 1.5 mL, 5.8 mmol) to a solution of tert-butyl 2-{(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}-2,9-diazaspiro[5.5]undecane-9-carboxylate (500 mg, 0.58 mmol) in dichloromethane (20 mL). After 2 hours at room temperature, concentrate to remove the solvent under reduced pressure to yield the title compound as a solid (480 mg, 0.57 mmol).

Workup

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

Sources & evidence

ORD record
ord-c7525dbc122a439588fc9de121e704e3
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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