Sulfamic Acid → HCID 58786122, compound

HRID 1375970Notes

Reaction equation

HRID 1375970 reaction equation
S(=O)(=O)(O)N.Cl([O-])=O.[Na+].[CH2:10]([O:17][C@@H:18]1[C@@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@H:22]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:21][C:19]1([C:50]1[CH:55]=[C:54]([CH:56]([O:59]C)[O:57]C)[CH:53]=[CH:52][C:51]=1[CH3:61])[OH:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O.O>[CH3:61][C:51]1[CH:52]=[CH:53][C:54]([C:56]([OH:59])=[O:57])=[CH:55][C:50]=1[C:19]1([OH:20])[C@H:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:23]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@@H:22]([CH2:41][O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[O:21]1

Participants

5

Reactant 3

HCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 58786243HCID 58786243, compound

Product 1

HCID 58786122HCID 58786122, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Sulfamic acid (0.4 g) and sodium chlorite (0.4 g) were added dropwise to a solution of 2,3,4,6-tetra-O-benzyl-1-C-[5-(dimethoxymethyl)-2-methylphenyl]-D-glucopyranose (2.4 g) in acetone-water (ratio: 5:1, 12 ml) at room temperature and the mixture was stirred for three hours. Acetone was evaporated from the reaction mixture and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 4-methyl-3-[(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]-2-hydroxytetrahydro-2H-pyran-2-yl]benzoic acid (1.5 g).

Workup

  1. customAcetone was evaporated from the reaction mixture and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6738b4ce71f14b01bacfe4b97b0a0587
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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