Methanol → (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 931678Notes

Reaction equation

HRID 931678 reaction equation
CO.C(N(CC)CC)C.Cl.Cl.C([O:15][C@@H:16]1[C@@H:53]([O:54]C(=O)C)[C@H:52]([O:58]C(=O)C)[C@@H:51]([CH2:62][O:63]C(=O)C)[O:50][C@H:17]1[O:18][C:19]1[C:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][C:37]4([CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)[CH2:36]3)=[CH:27][C:26]=2[CH3:46])=[C:22]([CH:47]([CH3:49])[CH3:48])[NH:21][N:20]=1)(=O)C>O>[O:18]([C:19]1[C:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][C:37]4([CH2:41][CH2:42][NH:43][CH2:44][CH2:45]4)[CH2:36]3)=[CH:27][C:26]=2[CH3:46])=[C:22]([CH:47]([CH3:49])[CH3:48])[NH:21][N:20]=1)[C@@H:17]1[O:50][C@H:51]([CH2:62][OH:63])[C@@H:52]([OH:58])[C@H:53]([OH:54])[C@H:16]1[OH:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 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 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 962WaterSolvent

Procedure

Add methanol (5 mL), triethylamine (3 mL), and water (3 mL) to 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 (480 mg, 0.24 mmol). After 18 hours (overnight) at room temperature, concentrate to dryness under reduced pressure. Purify the resulting residue 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 (50 mg, 0.08 mmol).

Workup

  1. concentrationconcentrate to dryness under reduced pressure
  2. customPurify the resulting residue by preparative HPLC method
  3. waithigh pH, 25% B for 4 min
  4. wait25-40 B % for 4 min @85 mL/min using

Sources & evidence

ORD record
ord-933a12d669d74726aa447efe0a24474a
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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