Hydrochloric Acid → HCID 59778412, compound
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:24])[O:11][CH2:12][C@@H:13]([N:15]([CH3:23])[C:16]([O:18]C(C)(C)C)=O)[CH3:14])=[CH:5][CH:4]=1)[CH3:2].[ClH:25].[CH2:26]([C:28]1[CH:33]=[CH:32][C:31](N=C=O)=[CH:30][CH:29]=1)C.CC[N:39](C(C)C)C(C)C>CO.C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:24])[O:11][CH2:12][C@@H:13]([N:15]([CH3:23])[C:16]([NH:39][CH2:26][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:25])=[O:18])[CH3:14])=[CH:7][CH:8]=1)[CH3:2]Participants
Procedure
To a solution of (S)-2-(methyl(tert-butoxycarbonyl)amino)propyl 4-ethylphenylcarbamate (105 mg, 0.27 mmol) in MeOH was added HCl (4M in dioxane, 0.2 mL, 0.81 mmol, 3 equiv.) and the mixture was stirred for 2 h. LC/MS indicated the reaction was complete and the mixture was concentrated under reduced pressure to give a crude oil, which was re-dissolved in THF. To this THF solution was added 4-ethylphenyl isocyanate (30 μL, 0.26 mmol) followed by DIEA (0.11 mL, 0.66 mmol, 2.5 equiv.). The reaction mixture was stirred for 2 h. LC/MS indicated the completion of the reaction. The mixture was filtered and the filtrate was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-2-(3-(2-chlorobenzyl)-1-methylureido)propyl 4-ethylphenylcarbamate (88.6 mg, 81% for two steps). LRMS (M+H+) m/z 404.1.
Workup
- concentrationthe mixture was concentrated under reduced pressure
- customto give a crude oil, which
- stirringThe reaction mixture was stirred for 2 h
- customthe completion of the reaction
- filtrationThe mixture was filtered
- customthe filtrate was purified on RP-HPLC
- additiona mixture of acetonitrile and H2O
Sources & evidence
- ORD record
- ord-5f7ee5b36ae84b819dff85881130292e
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071625B2
Reaction notes
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