Hydrochloric Acid → HCID 178427600, compound

HRID 1532755Notes

Reaction equation

HRID 1532755 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[NH:11]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:12]([C:30](N(OC)C)=[O:31])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:29])[NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].[Li]C1SC=CN=1.Cl.C1C[O:53]CC1>>[NH:11]([C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])[C@H:12]([C:30]([OH:53])=[O:31])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:29])[NH:18][S:19]([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:20])=[O:21].[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 9256ThiazoleHCID 178418339ButyllithiumHCID 178502742HCID 178502742, compoundHCID 178506781HCID 178506781, compound

Product 1

HCID 178427600HCID 178427600, compoundYield 84%

Procedure

To a solution of thiazole (2.5 g, 29 mmol) in THF (25 mL) at −78° C. was added n-BuLi (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. 1M 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. DCI-MS (M+H)+=496

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-66fa5cf00dfd4516a13bef8a1c2c96d3
Source dataset
uspto-grants-2001_03
Patent number
US06204268B1

Reaction notes

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