Hydrochloric Acid → HCID 178427600, compound

HRID 322014Notes

Reaction equation

HRID 322014 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[NH:6]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@H:7]([C:25](N(OC)C)=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[Li]C1SC=CN=1.Cl.C1C[O:48]CC1>CCCCCC>[NH:6]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[C@H:7]([C:25]([OH:48])=[O:26])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[NH:24])[NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:15])=[O:16].[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 9256ThiazoleHCID 178502742HCID 178502742, compoundHCID 178506781HCID 178506781, compound

Product 1

HCID 178427600HCID 178427600, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of thiazole (2.5 g, 29 mmol) in THF (25 mL) at −78° C. was added n-Budi (1.6 M in hexane, 19 mL) dropwise. The mixture was stirred for 30 minutes. Then a solution of Boc-Arg(Tos)N(Me)OMe, from Example 1, (1.7 g, 3.6 mmol) in THF (50 mL) was added to the lithiothiazole mixture at −78° C. The solution was stirred for 2 hours. 1 M HCl (30 mL) was added to the reaction mixture and warmed to room temperature. The mixture was extracted with EtOAc (100 mL). The organic layer was washed with sat NaCl (30 mL), dried over MgSO4, filtered and evaporated. The crude oily residue was purified by flash column chromatography over SiO2 (50% EtOAc in CH2Cl2) to give Boc-Arg(Tos)-thiazole, shown above, (1.5 g, 84% yield) as a powder.

Workup

  1. stirringThe solution was stirred for 2 hours
  2. extractionThe mixture was extracted with EtOAc (100 mL)
  3. washThe organic layer was washed with sat NaCl (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude oily residue was purified by flash column chromatography over SiO2 (50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-b9814d7217b448f1b1c56b6a7f547d99
Source dataset
uspto-grants-2001_04
Patent number
US06211183B1

Reaction notes

Loading…