Phosphoric Acid → HCID 42637931, compound

HRID 2238338Notes

Reaction equation

HRID 2238338 reaction equation
[CH2:1]([C@H:8]([NH:39][C:40](=[O:59])[C@H:41]([CH:56]([CH3:58])[CH3:57])[NH:42][C:43]([N:45]([CH2:47][C:48]1[N:49]=[C:50]([CH:53]([CH3:55])[CH3:54])[S:51][CH:52]=1)[CH3:46])=[O:44])[CH2:9][C@H:10]([O:29][CH:30](SCC(C)C)[CH:31]([CH3:33])[CH3:32])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][C:24]1[S:28][CH:27]=[N:26][CH:25]=1)=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:60](=[O:64])([OH:63])([OH:62])[OH:61].IN1C(=O)CCC1=O.C([O-])([O-])=O.[Na+:77].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.CO>[CH2:1]([C@H:8]([NH:39][C:40](=[O:59])[C@H:41]([CH:56]([CH3:58])[CH3:57])[NH:42][C:43]([N:45]([CH2:47][C:48]1[N:49]=[C:50]([CH:53]([CH3:55])[CH3:54])[S:51][CH:52]=1)[CH3:46])=[O:44])[CH2:9][C@H:10]([O:29][CH:30]([O:64][P:60]([O-:63])([O-:62])=[O:61])[CH:31]([CH3:33])[CH3:32])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][C:24]1[S:28][CH:27]=[N:26][CH:25]=1)=[O:21])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+:77].[Na+:77]

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 42637793HCID 42637793, compound

Product 1

HCID 42637931HCID 42637931, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing the product from Example 13A (0.888 g, 1.03 mmol), molecular sieves (4 Å, 3.5 g), and phosphoric acid (0.50 g) in DMF (20 mL) at 0° C. was added N-iodosuccinimide (0.46 g), and the mixture was stirred at 0° C. for 1 hour. To the cold reaction mixture was added 10% Na2CO3 to adjust the pH to 9, and the mixture was diluted with methanol, treated with 1 M Na2S2O3 until it was clear, and filtered to remove the solids. The solvent was evaporated, and the crude product was purified by HPLC using C18 column, eluting with a gradient starting with water and ending with methanol to give the product (0.49 g, 52% yield). 1H NMR (300 MHz, MeOH-d4), δ ppm 0.86-1.03 (m, 12H), 1.33-1.36 (m, 6H), 1.44-1.75 (m, 1H), 1.85-2.27 (m, 3H), 2.54-2.9 (m, 5H), 3.01 (s, 3H), 3.78-4.38 (m, 4H), 4.46-4.68 (m, 2H), 4.91-5.15 (m, 3H), 6.97-7.26 (m, 11H), 7.64-7.73 (m, 1H), 8.91-8.92 (m, 1H).

Workup

  1. customTo the cold reaction mixture
  2. filtrationfiltered
  3. customto remove the solids
  4. customThe solvent was evaporated
  5. customthe crude product was purified by HPLC
  6. washeluting with a gradient

Sources & evidence

ORD record
ord-25fda1375e4b4890afbebaf46d374400
Source dataset
uspto-grants-2010_05
Patent number
US07718633B2

Reaction notes

Loading…