Sodium Methoxide → HCID 86658294, compound

HRID 74859Notes

Reaction equation

HRID 74859 reaction equation
C([O:9][C@@H:10]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@H:14]([O:25]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[O:44][C@@H:45]1[C@@H:50]([CH2:51][O:52]C(=O)C2C=CC=CC=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:100]([CH2:101][O:102]C(=O)C3C=CC=CC=3)[O:99][C@@H:65]([O:66][NH:67][C:68](=[O:98])[CH2:69][O:70][CH:71]3[CH2:95][CH2:94][C@@:93]4([CH3:96])[CH:73]([CH2:74][CH2:75][C@@H:76]5[C@@H:92]4[CH2:91][CH2:90][C@@:89]4([CH3:97])[C@H:77]5[CH2:78][CH2:79][C@@H:80]4[C@H:81]([CH3:88])[CH2:82][CH2:83][CH2:84][CH:85]([CH3:87])[CH3:86])[CH2:72]3)[C@H:64]([O:111]C(=O)C3C=CC=CC=3)[C@H:63]2[O:120]C(=O)C2C=CC=CC=2)[C@H:47]([O:129]C(=O)C2C=CC=CC=2)[C@H:46]1[O:138]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO.C1COCC1>[C@H:11]1([O:44][C@@H:45]2[C@@H:50]([CH2:51][OH:52])[O:49][C@H:48]([O:61][C@@H:62]3[C@@H:100]([CH2:101][OH:102])[O:99][C@@H:65]([O:66][NH:67][C:68](=[O:98])[CH2:69][O:70][CH:71]4[CH2:95][CH2:94][C@@:93]5([CH3:96])[CH:73]([CH2:74][CH2:75][C@@H:76]6[C@@H:92]5[CH2:91][CH2:90][C@@:89]5([CH3:97])[C@H:77]6[CH2:78][CH2:79][C@@H:80]5[C@H:81]([CH3:88])[CH2:82][CH2:83][CH2:84][CH:85]([CH3:86])[CH3:87])[CH2:72]4)[C@H:64]([OH:111])[C@H:63]3[OH:120])[C@H:47]([OH:129])[C@H:46]2[OH:138])[O:12][C@H:13]([CH2:34][OH:35])[C@@H:14]([OH:25])[C@H:15]([OH:16])[C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866582952-(Cholestan-3-yloxy)acetamido 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside

Product 1

HCID 86658294HCID 86658294, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Amide 132 (345 mg, 175 μmol) was dissolved in MeOH/THF 1:1 (16 mL). NaOMe (500 μL of a 6M solution) was added and the solution was stirred at room temperature for 24 hrs. The mixture was neutralized with acidic resin and the solution filtered before the solvent was evaporated to yield the white solid product which was triturated with EtOAc and the solvent decanted (×3). The solid was dried under vacuum to yield 124 mg of the white solid product (76%) which was reacted on without further purification or characterisation.

Workup

  1. filtrationthe solution filtered before the solvent
  2. customwas evaporated
  3. customto yield the white solid product which
  4. customwas triturated with EtOAc
  5. customthe solvent decanted (×3)
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-831aeb3b6144463aa88f1405cacc0b6c
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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