Dimethylformamide → HCID 178511794, compound

HRID 355520Notes

Reaction equation

HRID 355520 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](C(OCC[Si](C)(C)C)=O)=[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:53]=[O:54])C>>[NH2:19][C@H:18]([C:53]([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:54])[CH2:17][C:16]1[N:15]=[CH:14][NH:13][CH:12]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 131720917HCID 131720917, compound

Product 1

HCID 178511794HCID 178511794, compound

Procedure

To a solution of HOBT (2.6 g, 19.3 mmol) in DMF (10 mL) was added Fmoc-His(Tr) (10.0 g, 16.1 mmol) followed by EDAC (3.7 g, 19.3 mmol). The mixture was stirred at room temperature for 20 minutes before adding a solution of Tyr(OBn)-CO2CH2CH2TMS (from Step 2 above, 5.8 g, 16.1 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature before partitioning between a mixture of water 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 974 (m+1).

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. custombefore partitioning between a mixture of water and 1:1 Et2O
  3. customThe layers were separated
  4. washthe organic phase was washed with saturated aqueous NaCl (4×20 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo
  7. customprovided an oil which
  8. customwas further purified by flash chromatography (SiO2, CHCl3 :MeOH eluent)

Sources & evidence

ORD record
ord-b79e875285da405b86a1b99ef10754d6
Source dataset
uspto-grants-1998_11
Patent number
US05830868

Reaction notes

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