Sodium Hydroxide → (2S,3R,4S,5S,6R)-2-((4-(4-((E)-4-(2,9-Diazaspiro[5.5]undecan-2-yl)but-1-en-1-yl)-2-methylbenzyl)-5-isopropyl-1H-pyrazol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 931674Notes

Reaction equation

HRID 931674 reaction equation
[OH-].[Na+].Cl.Cl.C([O:13][C@@H:14]1[C@@H:51]([O:52]C(=O)C2C=CC=CC=2)[C@H:50]([O:61]C(=O)C2C=CC=CC=2)[C@@H:49]([CH2:70][O:71]C(=O)C2C=CC=CC=2)[O:48][C@H:15]1[O:16][C:17]1[C:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][C:35]4([CH2:43][CH2:42][NH:41][CH2:40][CH2:39]4)[CH2:34]3)=[CH:25][C:24]=2[CH3:44])=[C:20]([CH:45]([CH3:47])[CH3:46])[NH:19][N:18]=1)(=O)C1C=CC=CC=1>CO>[O:16]([C:17]1[C:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][C:35]4([CH2:39][CH2:40][NH:41][CH2:42][CH2:43]4)[CH2:34]3)=[CH:25][C:24]=2[CH3:44])=[C:20]([CH:45]([CH3:47])[CH3:46])[NH:19][N:18]=1)[C@@H:15]1[O:48][C@H:49]([CH2:70][OH:71])[C@@H:50]([OH:61])[C@H:51]([OH:52])[C@H:14]1[OH:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 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 dihydrochloride

Product 1

HCID 71819574(2S,3R,4S,5S,6R)-2-((4-(4-((E)-4-(2,9-Diazaspiro[5.5]undecan-2-yl)but-1-en-1-yl)-2-methylbenzyl)-5-isopropyl-1H-pyrazol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 33.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium hydroxide (0.5 mL, 0.5 mmol, 1.0 M solution) to a solution of 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 (258 mg, 0.24 mmol) in methanol (2 mL). After 2 hours at 40° C., concentrate to remove the solvent under reduced pressure to give a residue, which is purified by preparative HPLC method: high pH, 25% B for 4 min, 25-40 B % for 4 min @85 mL/min using a 30×75 mm, 5 um C18XBridge ODB column, solvent A—H2O w NH4HCO3@pH 10, solvent B—MeCN to yield the title compound as a solid (46 mg, 0.08 mmol). MS (m/z): 598.8 (M+1), 596.8 (M−1).

Workup

  1. concentrationconcentrate
  2. customto remove the solvent under reduced pressure
  3. customto give a residue, which
  4. customis purified by preparative HPLC method
  5. waithigh pH, 25% B for 4 min
  6. wait25-40 B % for 4 min @85 mL/min using

Sources & evidence

ORD record
ord-1eaebab2ff634fc7bf426ad4234171d1
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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