Diisopropylethylamine → HCID 117958509, compound
Reaction equation
CCN(C(C)C)C(C)C.C(S[C:18](=[O:39])[CH2:19][C@H:20]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])C1C=CC=CC=1.Cl.[NH2:41][C@@H:42]([CH2:48][SH:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44]>CN(C=O)C.O>[C:35]([O:34][C:32]([NH:31][C@@H:20]([CH2:19][C:18]([NH:41][C@@H:42]([CH2:48][SH:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:39])[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[O:33])([CH3:36])([CH3:37])[CH3:38]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
DIPEA (0.098 ml, 0.563 mmol) was added to a solution of (S)-benzyl 4-(benzylthio)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate (Compound 5b-1) (201.5 mg, 0.469 mmol) and (R)-ethyl 2-amino-3-mercaptopropanoate hydrochloride (104.5 mg, 0.563 mmol) in DMF (1.2 ml) and water (0.3 ml), and the mixture was stirred at 50° C. for three hours. Water was then added to the reaction solution, and the mixture was purified by reverse phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=80/20→0/100) to afford (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-(((R)-1-ethoxy-3-mercapto-1-oxopropan-2-yl)amino)-4-oxobutanoate (Compound 5c-1) (133 mg, 67%).
Workup
- customthe mixture was purified by reverse phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=80/20→0/100)
Sources & evidence
- ORD record
- ord-d59a706486ee4f7099b2c9014a35a0cc
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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