Diisopropylethylamine → (S)-2-tert-Butoxycarbonylamino-3-[(5-chloro-thiophene-2-carbonyl)-amino]-propionic acid
Reaction equation
[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:4]([OH:6])=[O:5].CCN(C(C)C)C(C)C.[Cl:24][C:25]1[S:29][C:28]([C:30](Cl)=[O:31])=[CH:27][CH:26]=1>C(Cl)Cl>[C:11]([O:10][C:8]([NH:7][C@@H:3]([CH2:2][NH:1][C:30]([C:28]1[S:29][C:25]([Cl:24])=[CH:26][CH:27]=1)=[O:31])[C:4]([OH:6])=[O:5])=[O:9])([CH3:14])([CH3:13])[CH3:12]Participants
5
Procedure
Commercially available (S)-3-Amino-2-tert-butoxycarbonylamino-propionic acid (BOO-Dap-OH) (408 mg, 2 mmol) was suspended in 4 ml DCM and DIPEA (1.75 ml, 10 mmol). 5-Chloro-thiophene-2-carbonyl chloride (362 mg, 2 mmol) (described in WO 2005068456) in 4 ml DCM was added slowly and the mixture was stirred at RT for 2 h. The reaction was filtered and the solvent evaporated. The resulting solid (895 mg) was used without further purification in the next step.
Workup
- filtrationThe reaction was filtered
- customthe solvent evaporated
- customThe resulting solid (895 mg) was used without further purification in the next step
Sources & evidence
- ORD record
- ord-a0942b99eb52414894521a8ff2412898
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378092B2
Reaction notes
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