Water → HCID 11156230, compound

HRID 604582Notes

Reaction equation

HRID 604582 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][S:7]([NH:10][CH2:11][C:12]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:16][C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[N:14][N:13]1[C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])(=[O:9])=[O:8])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][CH2:4][CH2:5][CH2:6][S:7]([NH:10][CH2:11][C:12]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:16][C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:20])([CH3:21])[CH3:22])=[N:14][N:13]1[C:24](=[O:29])[C:25]([CH3:27])([CH3:28])[CH3:26])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86622488HCID 86622488, compound

Product 1

HCID 11156230HCID 11156230, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Next, the resulting N-[5-(3-azidopropanesulfonylamino-methyl)-4-(2,2-dimethylpropionyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide was dissolved in THF (53 mL), and water (10.6 mL) and triphenylphosphine (1.24 g, 4.73 mmol) were added, then the mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate were added, then the mixture was extracted with ethyl acetate. The organic layer was extracted with aqueous hydrochloric acid, and the aqueous layer was made basic by adding saturated aqueous sodium hydrogencarbonate, and then extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure to give N-[5-(3-aminopropanesulfonylaminomethyl)-4-(2,2-dimethylpropionyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide (1.29 g, 89%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, and water and saturated aqueous sodium hydrogencarbonate
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic layer was extracted with aqueous hydrochloric acid
  5. additionby adding saturated aqueous sodium hydrogencarbonate
  6. extractionextracted with ethyl acetate
  7. concentrationThe resulting organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e76f4019d4fb4fc793146dfd8e4e866a
Source dataset
uspto-grants-2011_03
Patent number
US07910611B2

Reaction notes

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