Diphenylphosphinic chloride → HCID 69878470, compound

HRID 1838088Notes

Reaction equation

HRID 1838088 reaction equation
C1C=CC(P(Cl)(C2C=CC=CC=2)=O)=CC=1.C([O:19][C:20]1[C:21]([CH3:29])=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([OH:25])=O)(=O)C.[C:30]([NH:34][C:35]([C@@H:37]1[C:41]([CH3:43])([CH3:42])[S:40][CH2:39][N:38]1[C:44](=[O:58])[C@@H:45]([OH:57])[C@@H:46]([NH2:56])[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=1)=[O:36])([CH3:33])([CH3:32])[CH3:31]>CCOC(C)=O>[C:30]([NH:34][C:35]([C@@H:37]1[C:41]([CH3:42])([CH3:43])[S:40][CH2:39][N:38]1[C:44](=[O:58])[C@@H:45]([OH:57])[C@@H:46]([NH:56][C:23](=[O:25])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([OH:19])[C:21]=1[CH3:29])[CH2:47][C:48]1[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=1)=[O:36])([CH3:31])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 73910Diphenylphosphinic chlorideHCID 37985573-Acetoxy-2-methylbenzoic acidHCID 69879176HCID 69879176, compound

Product 1

HCID 69878470HCID 69878470, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

DPP-Cl (43 μl) and TEA (31 μl) were added to a solution of 3-acetoxy-2-methylbenzoic acid (41 mg) in EtOAc (2 ml), and the mixture was stirred for one hour. After the addition of the compound obtained in Step 2 (85 mg) and TEA (34 μl), the mixture was stirred overnight. The reaction mixture was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl. After concentration, MeOH (1.5 ml) and 1N NaOH (300 μl) were added. After stirring for one hour, IN HCl was added to make the reaction mixture acidic. The resulting mixture was extracted with EtOAc. The extract was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl, dried over MgSO4, filtered and concentrated. The residue was recrystallized from a mixture of EtOAc and n-hexane to obtain the title compound (90 mg, 81%).

Workup

  1. stirringthe mixture was stirred overnight
  2. washThe reaction mixture was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl
  3. concentrationAfter concentration, MeOH (1.5 ml) and 1N NaOH (300 μl)
  4. additionwere added
  5. stirringAfter stirring for one hour, IN HCl
  6. additionwas added
  7. extractionThe resulting mixture was extracted with EtOAc
  8. washThe extract was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was recrystallized from a mixture of EtOAc and n-hexane

Sources & evidence

ORD record
ord-c7b0c5f53aea4a22ae767146e9be0108
Source dataset
uspto-grants-2004_01
Patent number
US06673772B2

Reaction notes

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