Hydrochloric Acid → HCID 11038164, compound

HRID 1721493Notes

Reaction equation

HRID 1721493 reaction equation
C(OC(N[CH2:9][P:10]([CH2:15][NH:16][C:17](OC(C)(C)C)=O)(=[O:14])[O:11][CH2:12][CH3:13])=O)(C)(C)C.Cl.[C:25]1([C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[NH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[C:33]1([C:31]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:32][CH2:9][P:10]([CH2:15][N:16]=[C:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:14])[O:11][CH2:12][CH3:13])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 136809Benzophenone imineHCID 10926216HCID 10926216, compound

Product 1

HCID 11038164HCID 11038164, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The tert-butoxycarbonyl protective group is removed from the ethyl phosphinate 2 (100 mg; 0.28 mmol) using 3N methanolic hydrochloric acid (30 ml) (check via DC). The reaction solution is evaporated under reduced pressure. Diphenylmethanimine (0.100 ml; 0.60 mmol) is added dropwise to the suspension of the crude product in methylene chloride (20 ml) under an atmosphere of nitrogen. The reaction solution is filtered after being stirred for 16 hours at room temperature. The filtrate is evaporated under reduced pressure. The crude product is taken up in ether, filtered and extracted with water (2×20 ml). The organic phase is dried over Na2SO4 and evaporated under reduced pressure. The diphenylmethylene phosphinate 3 (71 mg, 53% of theory) is obtained after purification on silica gel using column chromatography (ethyl acetate/heptane=1/1).

Workup

  1. customThe reaction solution is evaporated under reduced pressure
  2. filtrationThe reaction solution is filtered
  3. customThe filtrate is evaporated under reduced pressure
  4. filtrationfiltered
  5. extractionextracted with water (2×20 ml)
  6. dry with materialThe organic phase is dried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-103c84020c57425bbf2c96265b4e8592
Source dataset
uspto-grants-1996_04
Patent number
US05510504

Reaction notes

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