Dichloromethane → 3-({[(2S)-2-amino-3-methoxy-3-oxopropyl]carbamoyl}amino)benzene-1-sulfonic acid
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:16])[C@@H:5]([NH:8]C(OC(C)(C)C)=O)[CH2:6][NH2:7].[NH2:17][C:18]1[CH:19]=[C:20]([S:24]([OH:27])(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.C(Cl)Cl.[O:31]1CCC[CH2:32]1>>[NH2:8][C@H:5]([C:4]([O:3][CH3:2])=[O:16])[CH2:6][NH:7][C:32]([NH:17][C:18]1[CH:19]=[C:20]([S:24]([OH:27])(=[O:25])=[O:26])[CH:21]=[CH:22][CH:23]=1)=[O:31]Participants
Procedure
To 127 mg (0.5 mmol) of (2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoic acid methylester hydrochloride, 87 mg (0.5 mmol) of 3-aminobenzenesulfonic acid and 97 mg (0.6 mmol) of N,N-carbonyl diimidazole, 1 ml of methylene chloride and 1 ml of tetrahydrofuran were added and stirred at room temperature overnight. After distilling the solvent away, purification was carried out using purification step A to obtain a crude purified substance of the title compound in protected form. To the obtained crude purified substance, 1 ml of methylene chloride and 1 ml of trifluoroacetic acid were added and stirred at room temperature for 5 hours. After distilling the solvent away, purification was carried out by purification step A to obtain the title compound.
Workup
- distillationAfter distilling the solvent away
- custompurification
- custompurification step A
- customto obtain a crude
- custompurified substance of the title compound in protected form
- customTo the obtained crude
- custompurified substance, 1 ml of methylene chloride and 1 ml of trifluoroacetic acid
- additionwere added
- stirringstirred at room temperature for 5 hours
- distillationAfter distilling the solvent away
- custompurification
- customwas carried out by purification step A
Sources & evidence
- ORD record
- ord-b30f6ad8750846c4b5808d8420fe6ddb
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150505B2
Reaction notes
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