Hydrochloric Acid → HCID 178427600, compound
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]1Participants
7
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 min. Then a solution of Boc-Arg(Tos)-N(Me)OMe (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 h. 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 over silica gel(50% EtOAc in CH2Cl2) to give Boc-Arg(Tos)-Thiazole (1.5 g, 84% yield) as a white powder. DCI-MS (M+H)+=496
Workup
- stirringThe solution was stirred for 2 h
- extractionThe mixture was extracted with EtOAc (100 mL)
- washThe organic layer was washed with sat. NaCl (30 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe crude oily residue was purified by flash column over silica gel(50% EtOAc in CH2Cl2)
Sources & evidence
- ORD record
- ord-55e12fc635c64d4a866fa175dd9c2f08
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197748B1
Reaction notes
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