Water → HCID 13588529, compound

HRID 1534329Notes

Reaction equation

HRID 1534329 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH:23]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:24][C:25](=[CH2:41])[CH2:26][C:27]([NH:38][CH:39]=[O:40])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N+]=[N-].O>O1CCCC1>[NH2:20][CH:23]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:24][C:25](=[CH2:41])[CH2:26][C:27]([NH:38][CH:39]=[O:40])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 13588527HCID 13588527, compound

Product 1

HCID 13588529HCID 13588529, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.9 g of triphenylphosphine were added to a solution of 13 g of the product of Step 3 in 250 ml of tetrahydrofuran at approximately -5° C. and the mixture was stirred for 5 hours at room temperature. 8.5 ml of water were added and the mixture was stirred for 24 hours at room temperature. The tetrahydrofuran was evaporated off and the residue was taken up in methylene chloride. The mixture was poured into ice-cold 2N hydrochloric acid, followed by extraction with 2N hydrochloric acid, neutralization with sodium bicarbonate and extraction with methylene chloride. The extract was washed with saline solution, dried and evaporated to dryness to obtain 10 g of the expected product melting at 50° C. after crystallization from isopropyl ether.

Workup

  1. stirringthe mixture was stirred for 24 hours at room temperature
  2. customThe tetrahydrofuran was evaporated off
  3. additionThe mixture was poured into ice-cold 2N hydrochloric acid
  4. extractionfollowed by extraction with 2N hydrochloric acid, neutralization with sodium bicarbonate and extraction with methylene chloride
  5. washThe extract was washed with saline solution
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8944039a56204878bdd8ea540d24a9ac
Source dataset
uspto-grants-1992_02
Patent number
US05089476

Reaction notes

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