N,N'-Dimethylethylenediamine → HCID 68554951, compound
Reaction equation
[NH2:1][C:2]1[C:31](I)=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33].[NH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39].CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[NH2:1][C:2]1[C:31]([N:34]2[CH2:38][CH2:37][CH2:36][C:35]2=[O:39])=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 115 °C
Procedure
To a solution of (3aR,7S,7aS)-7-(4-amino-3-fluoro-5-iodo-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (0.10 g, 0.17 mmol), 2-pyrrolidin-one (0.02 mL, 0.26 mmol) and N,N′-dimethylethylenediamine (0.002 mg, 0.017 mmol) in dioxane (10 mL) was added CuI (0.002 g, 0.009 mmol) and K3PO4 (0.077 g, 0.36 mmol) and the reaction mixture was heated at 115° C. for 4 h. The reaction mixture was filtered over Celite and concentrated. The crude product was purified on the flashmaster (10 g silicagel, cyclohexane-EtOAc 100:0 to 0:100) to yield the title compound as a yellow solid, which was directly used as such in the next step: HPLC RtC=4.728 min; ESIMS [M+H]+=544.
Workup
- filtrationThe reaction mixture was filtered over Celite
- concentrationconcentrated
- customThe crude product was purified on the flashmaster (10 g silicagel, cyclohexane-EtOAc 100:0 to 0:100)
Sources & evidence
- ORD record
- ord-6ad5d7d75bbe4d73a0a7e2568e5978a0
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093406B2
Reaction notes
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