p-Toluenesulfonic acid → HCID 131717379, compound

HRID 1196727Notes

Reaction equation

HRID 1196727 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17]C1C=CC(S(O)(=O)=O)=CC=1.[NH:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@@H:29]([C:33]([OH:35])=O)[CH:30]([CH3:32])C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+]>ClCCl.O>[NH:28]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[C@H:29]([C:33]([NH:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:35])[CH2:30][CH2:32][CH3:17]

Participants

10

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6451313Benzyl L-leucinate

Product 1

HCID 131717379HCID 131717379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Leu-OBzl.p-TsOH(2.06 g), Boc-DVal (1.09 g), HOBT.H2O(0.80 g) and N-methylmorpholine(0.55 ml) in dichloromethane(10 ml) was added EDCI HCl(1.01 g) under ice cooling. The resulting mixture was stirred at room temperature for 5 h. Saturated NaHCO3 (10ml) was added, and the mixture was extracted with dichloromethane(50 ml×3). The combined organic layers were dried over MgSO4 and filtered. The solvent was evaporated under reduced pressure. The residue was purified by dry column flash chromatography on silica gel(Merck, KIESELGEL 60) with hexane/EtOAc(2/1) for elution to give Boc-nVal-Leu-OBzl(2.03 g) as a colorless powder. The dipeptide(1.47 g) was added by portions to TFA(3.5 ml) under ice cooling. The mixture was stirred under ice cooling for 30 min and concentrated in vacuo. To the residue was added saturated NaHCO3 (10 ml) and the mixture was extracted with dichloromethane(50 ml×3).

Workup

  1. extractionthe mixture was extracted with dichloromethane(50 ml×3)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified
  6. dry with materialby dry column flash chromatography on silica gel(Merck, KIESELGEL 60) with hexane/EtOAc(2/1)
  7. washfor elution

Sources & evidence

ORD record
ord-88fb323196484aa6b5e6c456d30535e5
Source dataset
uspto-grants-1992_05
Patent number
US05114918

Reaction notes

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