Potassium Carbonate → HCID 178451266, compound
Reaction equation
Cl.C(CN(S(C1C=C2C(C(Cl)=CN=C2NC(N)=N)=CC=1)(=O)=O)CC(O)=O)(O)=O.C([O-])([O-])=O.[K+].[K+].Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].[C:44]([O:48][C:49](=[O:70])[CH2:50][NH:51][S:52]([C:55]1[CH:64]=[C:63]2[C:58]([C:59]([Cl:69])=[CH:60][N:61]=[C:62]2[NH:65][C:66]([NH2:68])=[NH:67])=[CH:57][CH:56]=1)(=[O:54])=[O:53])([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.CCOC(C)=O>[C:40]([O:39][C:37](=[O:38])[CH2:36][N:51]([CH2:50][C:49]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:70])[S:52]([C:55]1[CH:64]=[C:63]2[C:58]([C:59]([Cl:69])=[CH:60][N:61]=[C:62]2[NH:65][C:66]([NH2:68])=[NH:67])=[CH:57][CH:56]=1)(=[O:53])=[O:54])([CH3:43])([CH3:42])[CH3:41]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
N-(Carboxymethyl)-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine hydrochloride ##STR31## Anhydrous K2CO3 (88 mg, 0.64 mmol) and then t-butyl bromoacetate (56 μL, 0.38 mmol) were added to a stirred solution of N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine t-butyl ester (132 mg, 0.33 mmol) in DMF (2.0 mL) and the mixture was stirred at 23° C. for 18 h. The mixture was diluted with EtOAc (300 mL), washed with brine (150 mL), water (200 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using pentane-EtOAc (80:20 to 50:50) as eluant to give N-(t-butoxycarbonylmethyl)-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]glycine t-butyl ester (101 mg, 0.19 mmol) as a pale yellow foam.
Workup
- washwashed with brine (150 mL), water (200 mL)
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customThe residue was purified by column chromatography upon silica gel
Sources & evidence
- ORD record
- ord-319e8c9e0d5049299f20110f1252277c
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06093731
Reaction notes
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