Sodium Methoxide → HCID 21308801, compound

HRID 442631Notes

Reaction equation

HRID 442631 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1[N:24]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])(=[O:3])[CH3:2].C[O-].[Na+]>CO.C[O-].[Na+].CO>[C:1]([NH:4][C@@H:5]1[C@@H:10]([OH:11])[C@@H:9]([OH:15])[C@@H:8]([CH2:19][OH:20])[O:7][C@@H:6]1[N:24]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[C:25](=[O:32])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 21308802HCID 21308802, compound

Product 1

HCID 21308801HCID 21308801, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23694274Sodium methanolate methanolSolvent

Procedure

Compound 49 (1.4 g) was dissolved in methanol to which sodium methoxide-methanol solution was added dropwise to pH 11.0 and stirred at room temperature. The pH was adjusted to 11.0 with fresh sodium methoxide solution several times until the pH was stable (approximately 1 hr). The reaction mixture was acidified with Dowex-H type resin and the resin was removed from the solution by filtration. The solvent was removed from the filtrate under vacuum to give 2-acetamido-1-(N-CBZ-6-aminohexanamido)-1,2-dideoxy-a-D-galactopyranose, 50, as a gum (630 mg). 1H NMR (CDCl3): 1H NMR (CD3OD): 7.35-7.40, s, 5H, C6H5CH2 -; 5.78-5.8,m, 1H; 5.12, s, 2H, C6H5CH2; 4.45-3.8, m, 6H; 3.65-3.6, m, 1H; 2.22,s, 3H; NHCOCH3; 1.5-1.7, m, 10H.

Workup

  1. additionwas added dropwise to pH 11.0
  2. custom(approximately 1 hr)
  3. customthe resin was removed from the solution by filtration
  4. customThe solvent was removed from the filtrate under vacuum

Sources & evidence

ORD record
ord-61dae75f7eac488d9d1ece6e41da5f0c
Source dataset
uspto-grants-1999_04
Patent number
US05891862

Reaction notes

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