Hydrochloric Acid → HCID 178427600, compound

HRID 1107836Notes

Reaction equation

HRID 1107836 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. is added n-BuLi (1.6 M in hexane, 19 mL) dropwise. The mixture is 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) is added to the lithiothiazole mixture at -78° C. The solution is stirred for 2 hours. 1M HCl (30 mL) is added to the reaction mixture and warmed to room temperature. The mixture is extracted with EtOAc (100 mL). The organic layer is washed with sat. NaCl (30 mL), dried over MgSO4, filtered and evaporated. The crude oily residue is purified by flash column 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 is stirred for 2 hours
  2. extractionThe mixture is extracted with EtOAc (100 mL)
  3. washThe organic layer is washed with sat. NaCl (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude oily residue is purified by flash column over SiO2 (50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-db2854121e534366b492f11d5150a3bd
Source dataset
uspto-grants-2000_05
Patent number
US06063794

Reaction notes

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