Acetic Anhydride → HCID 10000206, compound

HRID 2118633Notes

Reaction equation

HRID 2118633 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C@@H:8]1([C:17]2[S:18][CH:19]=[C:20]([C:22]([NH2:24])=[O:23])[N:21]=2)[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]1[OH:10]>N1C=CC=CC=1>[C:9]([O:10][C@@H:9]1[C@H:11]([O:12][C:11](=[O:12])[CH3:13])[C@@H:13]([CH2:15][O:16][C:5](=[O:7])[CH3:6])[O:14][C@H:8]1[C:17]1[S:18][CH:19]=[C:20]([C:22]([NH2:24])=[O:23])[N:21]=1)(=[O:10])[CH3:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 457954Tiazofurin

Product 1

HCID 10000206HCID 10000206, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2.0 ml) was added to an ice-cold solution of compound 1 (1.04 g, 4 mmol) in anhydrous pyridine (16 ml) and the reaction solution was stirred at room temperature for 17 h. The solvent was evaporated in vacuo, the residue was dissolved in ethyl acetate, and the solution was washed with water and dried (MgSO4). The ethyl acetate portion was evaporated in vacuo and the residue thus obtained was crystalized from water to provide 1.4 g (90%) of compound 2 as white needles; mp 103° C.; 1H NMR (CDCl3) 2.1 (3 s, 9, tri-O-acetyl), 6.2 and 7.15 [pair of s(br), 2, CONH2 ], 8.2 (s, 1, H5). Anal. (C15H18N2O8S) C, H, N, S.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washthe solution was washed with water
  4. dry with materialdried (MgSO4)
  5. customThe ethyl acetate portion was evaporated in vacuo
  6. customthe residue thus obtained
  7. customwas crystalized from water

Sources & evidence

ORD record
ord-7b7e8b85e8ca4117af8f578a309f6a9d
Source dataset
uspto-grants-1987_07
Patent number
US04680285

Reaction notes

Loading…