Hydrochloric Acid → HCID 69753596, compound

HRID 583953Notes

Reaction equation

HRID 583953 reaction equation
[N:1]([CH:4]1[CH2:8][N:7]([C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:14][CH:13]=2)[C@H:6]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>O1CCCC1>[NH2:1][CH:4]1[CH2:8][N:7]([C:9](=[O:27])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])=[CH:16][CH:17]=2)[C@H:6]([C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 86591772HCID 86591772, compound2×

Product 1

HCID 69753596HCID 69753596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.2 g of benzyl 4-azido-1-[3-(4-tert-butyloxycarbonylaminomethylphenyl)propionyl]prolinate (starting material B3) are dissolved in 50 ml of tetrahydrofuran, and 3.52 g of triphenylphosphine are then added a little at a time, as a result of which a clear evolution of gas can be observed. After 4 h of stirring at RT, 10 ml of water are added, and the mixture is stirred at RT for 6 days. 12.5 ml of 1N hydrochloric acid solution are added, and the mixture is then extracted twice with ethyl acetate. Using 13 ml of 1N sodium hydroxide solution, the aqueous phase is made slightly alkaline, and the phase is then extracted three times with a mixture of ether/methanol (8:2). The extract is dried over magnesium sulfate and then concentrated, and the residue is dried under high vacuum. This gives 2.22 g of the title compound as a viscous oil. The mass spectrum shows the molecular peaks MH+, MNa+ and M2H+ at 482, 504 and 962 Da, respectively.

Workup

  1. customas a result of which a clear evolution of gas
  2. stirringthe mixture is stirred at RT for 6 days
  3. extractionthe mixture is then extracted twice with ethyl acetate
  4. extractionthe phase is then extracted three times
  5. additionwith a mixture of ether/methanol (8:2)
  6. dry with materialThe extract is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-e504b9754c274c63b343e6ca40957e2e
Source dataset
uspto-grants-2005_08
Patent number
US06924305B2

Reaction notes

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