Dimethylformamide → HCID 178511794, compound
Reaction equation
C1C=CC2N([OH:10])N=NC=2C=1.C[CH2:12][N:13]=[C:14]=[N:15][CH2:16][CH2:17][CH2:18][N:19](C)C.[NH2:22][C@H:23]([C:39](NCCCOC1C=CC=CC=1)=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31]CC2C=CC=CC=2)=[CH:27][CH:26]=1.CN([CH:55]=[O:56])C>>[NH2:19][C@H:18]([C:55]([NH:22][C@H:23]([C:39]([OH:40])=[O:10])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)=[O:56])[CH2:17][C:16]1[N:15]=[CH:14][NH:13][CH:12]=1Participants
Procedure
To a solution of HOBT (0.48 g, 3.5 mmol) in DMF (10 mL) was added Fmoc-D-His(Tr)-CO2H (2.0 g, 3.2 mmol) followed by EDAC (0.67 g, 3.5 mmol). The mixture was stirred at room temperature for 20 minutes before adding a solution of Tyr(OBn)-CONH(CH2)3OPh (from Step 2 above, 1.4 g, 3.2 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature before partitioning between a mixture of water (20 mL) and 1:1 Et2O:EtOAc (50 mL). The layers were separated, and the organic phase was washed with saturated aqueous NaCl (4×20 mL) and dried (MgSO4). Filtration and concentration in vacuo provided an oil which was further purified by flash chromatography (SiO2, CHCl3 : MeOH eluent) to give the protected His-Tyr dipeptide; FAB-MS 1006 (m).
Workup
- stirringThe mixture was stirred overnight at room temperature
- custombefore partitioning between a mixture of water (20 mL) and 1:1 Et2O
- customThe layers were separated
- washthe organic phase was washed with saturated aqueous NaCl (4×20 mL)
- dry with materialdried (MgSO4)
- filtrationFiltration and concentration in vacuo
- customprovided an oil which
- customwas further purified by flash chromatography (SiO2, CHCl3 : MeOH eluent)
Sources & evidence
- ORD record
- ord-2965a40fd2ea41c282eab66bcb0d05d9
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05830868
Reaction notes
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