Sulfuric Acid → HCID 3011031, compound

HRID 1379390Notes

Reaction equation

HRID 1379390 reaction equation
S(=O)(=O)(O)O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[C:17]([NH:27][C@H:28]([C:32]([NH:34][CH:35]([C:39]([F:69])([F:68])[CH:40]([OH:67])[CH:41]([NH:49][C:50](=[O:66])[C@H:51]([CH:63]([CH3:65])[CH3:64])[NH:52][C:53]([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54])[CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)[CH:36]([CH3:38])[CH3:37])=[O:33])[CH:29]([CH3:31])[CH3:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C(O)(=O)C>[C:17]([NH:27][C@H:28]([C:32]([NH:34][CH:35]([C:39]([F:68])([F:69])[C:40](=[O:67])[CH:41]([NH:49][C:50](=[O:66])[C@H:51]([CH:63]([CH3:65])[CH3:64])[NH:52][C:53]([O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)=[O:54])[CH2:42][CH:43]1[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1)[CH:36]([CH3:38])[CH3:37])=[O:33])[CH:29]([CH3:31])[CH3:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 3011030HCID 3011030, compound

Product 1

HCID 3011031HCID 3011031, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of oxidant was prepared as follows: to 392 mg of sulfuric acid was added 5 ml of acetic acid and 298 mg of sodium dichromate. To a solution of 150 mg of the resultant compound of Example 182 in 10 ml of acetic acid was added 2 ml of the oxidant. After stirring at ambient temperature for 1 hr, the acetic acid was removed under vacuum and the residue was dissolved in 50 ml of ethyl acetate and washed with 30 ml of water. The aqueous layer was extracted with ethyl acetate (2×40 ml) and the combined ethyl acetate solution was dried, filtered and concentrated. The crude product was purified by silica gel column chromatography (10% EtOAc/CH2Cl2) to give 120 mg of the desired compound (80%). Mass spectrum: (M+H)+ =743. 1H NMR (CDCl3): d 0.85-0.98 (m, 18H), 3.90-4.02 (m, 2H), 460 (m, 1H), 5.35 (br d, 1H), 6.10 (br d, 1H), 6.20 (br d, 1H), 7.35 (m, 10H).

Workup

  1. customA solution of oxidant was prepared
  2. customthe acetic acid was removed under vacuum
  3. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  4. washwashed with 30 ml of water
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×40 ml)
  6. dry with materialthe combined ethyl acetate solution was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography (10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-1a8939931b1f4305a0b4f2688d4c96d4
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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