Ethyl Acetate → HCID 70060223, compound
Reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=1.C(OCC)(=O)C>CN(C=O)C.O>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:18])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
A solution of the product from Example G (1.0 g, 2.18 mmol) was dissolved in DMF and cooled to 0° C. The resulting solution treated with NaH (2.18 mmol) and was stirred for 1 hour at 0° C. and treated with α-bromo-p-tolunitrile (0.45 g, 2.30 mmol). The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into a separatory funnel containing ethyl acetate (50 mL) and water (50 mL) and shaken. The organic phase was separated and washed with brine, dried, and concentrated to give the title compound (0.76 g, 61%).
Workup
- temperatureThe reaction mixture was warmed to room temperature
- stirringstirred overnight
- additionThe reaction mixture was poured into a separatory funnel
- stirringshaken
- customThe organic phase was separated
- washwashed with brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-709ab36c8b0c4de7abc6149d535c4138
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06423689B1
Reaction notes
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