Reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[NH2:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.Cl>C1COCC1.CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
7
Procedure
To a solution of Z-PheOH (0.207 g, 0.69 mmol) in THF (4 mL), cooled to -20° C., were added NMM (76 uL, 0.69 mmol) and IBCF (90 uL, 0.69 mmol). After 10 minutes, a chilled (-10° C.) solution of PheCH2F hydrochloride (0.15 g, 0.69 mmol) in DMF (1 mL) was added, followed by NMM (76 uL, 0.69 mmol). The mixture was stirred for 30 minutes. 1M HCl (5 mL) was added. The solution was extracted with ethyl acetate (30 mL), washed with saturated aqueous NaHCO3 (6 mL), brine (4 mL), dried over MgSO4, filtered, and evaporated to dryness. The residue was crystallized from ethyl acetate/hexane, yielding 0.22 (53%) of Z-Phe-PheCH2F.
Workup
- additionwas added
- extractionThe solution was extracted with ethyl acetate (30 mL)
- washwashed with saturated aqueous NaHCO3 (6 mL), brine (4 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was crystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-b056866b65314ff4a2dd2e3080fdd500
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05210272
Linked notes
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