Thioglycerol → HCID 178472730, compound

HRID 576568Notes

Reaction equation

HRID 576568 reaction equation
[CH2:1]([O:3][C:4](=[O:58])[CH2:5][N:6]([C:8](=[O:57])[C@@H:9]([NH:25][C:26](=[O:56])[C@@H:27]([NH:52][C:53](=[O:55])[CH3:54])[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:46])([CH3:45])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:36])=[O:35])[CH2:10][N:11]([CH3:24])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH3:7])[CH3:2].C([O-])([O-])=O.[K+].[K+].SCC(CO)O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:58])[CH2:5][N:6]([C:8](=[O:57])[C@@H:9]([NH:25][C:26](=[O:56])[C@@H:27]([NH:52][C:53](=[O:55])[CH3:54])[CH2:28][CH2:29][CH2:30][NH:31]/[C:32](/[NH2:51])=[N:33]\[S:34]([C:37]1[C:38]([CH3:50])=[C:39]([CH3:49])[C:40]2[O:44][C:43]([CH3:46])([CH3:45])[CH2:42][C:41]=2[C:47]=1[CH3:48])(=[O:36])=[O:35])[CH2:10][NH:11][CH3:24])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 7291ThioglycerolHCID 11430Potassium CarbonateHCID 178472731HCID 178472731, compound

Product 1

HCID 178472730HCID 178472730, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound G (5.5 g, 6.5 mmol) in DMF (21 mL) at ambient temperature was added K2CO3 (8.9 g, 64.5 mmol) followed by thioglycerol (5.6 mL, 64.5 mmol). The reaction mixture was stirred at ambient temperature for 1 h, filtered off and DMF was removed in vacuo. The residue was diluted with water (500 mL) and extracted with EtOAc (2×300 mL) and CHCl3 (2×300 mL). Combined organic layers were dried and removal of the solvents in vacuo afforded the crude product. The crude product was purified by flash chromatography eluting with EtOAc followed by 10% MeOH in CHCl3 to afford compound H (1.3 g, 30%). LC-MS [M+H] 668.3 (C30H49N7O8S+H, calc: 667.8). Purity >95% (UV/254 nm).

Workup

  1. filtrationfiltered off
  2. customDMF was removed in vacuo
  3. additionThe residue was diluted with water (500 mL)
  4. extractionextracted with EtOAc (2×300 mL) and CHCl3 (2×300 mL)
  5. customCombined organic layers were dried
  6. customremoval of the solvents in vacuo
  7. customafforded the crude product
  8. customThe crude product was purified by flash chromatography
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-cd87975301a8442bbaf3d3d6986f2e11
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

Loading…