Triethylamine → HCID 131728376, compound

HRID 1160042Notes

Reaction equation

HRID 1160042 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH2:12])=[O:11].[NH:16]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:17]([C:26](ON1C(=O)CCC1=O)=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=1>CN(C=O)C>[NH:16]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:17]([C:26]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH2:12])=[O:11])=[O:27])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([I:25])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111306L-ProlinamideHCID 131728377HCID 131728377, compound

Product 1

HCID 131728376HCID 131728376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (163.8 ml, 1.17 mmol) was added to a solution of H-ProNH2*HCl (118.5 mg, 0.782 mmol) in dry DMF (10 ml). Boc-p-Iodo-Phe-OSu (0.42 g, 0.86 mmol) was added in one portion and the mixture stirred for 16 h under an argon atmosphere. The solvent was evaporated and the residue treated in a standard way, i.e. the residue was partitioned between ethylacetate (60 ml) and 0.3N KHSO4 solution (10 ml). The organic layer was further washed with saturated NaCHO3 solution (10 ml), water (10 ml)and brine (5 ml). The solution was dried and evaporated at reduced pressure.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue treated in a standard way, i.e. the residue
  3. customwas partitioned between ethylacetate (60 ml) and 0.3N KHSO4 solution (10 ml)
  4. washThe organic layer was further washed with saturated NaCHO3 solution (10 ml), water (10 ml)and brine (5 ml)
  5. customThe solution was dried
  6. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-db1d51dffae54057956426bd7a1cd30c
Source dataset
uspto-grants-2010_10
Patent number
US07816325B2

Reaction notes

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