Water → Boc-Ile-Pro-OBzl

HRID 1725094Notes

Reaction equation

HRID 1725094 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C.[NH:23]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:24]([C:29]([OH:31])=O)[C@H:25]([CH2:27][CH3:28])[CH3:26].O.[NH:40]1[CH2:54][CH2:53][CH2:52][C@@H:41]1[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43].Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:23]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:24]([C:29]([N:40]1[CH2:54][CH2:53][CH2:52][C@H:41]1[C:42]([O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:43])=[O:31])[C@H:25]([CH2:27][CH3:28])[CH3:26]

Participants

8

Reactant 6

HCID 962Water2×HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 14306235Boc-Ile-Pro-OBzlYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

While cooling on ice, DCC (1.24 g, 6.0 mmol) and triethylamine (0.70 ml, 4.0 mmol) were added to DMF (10 ml) containing Boc-L-Ile-OH.1/2 H2O (1.39 g, 6.0 mmol), H-D-Pro-OBzl-HCl (956 mg, 4.0 mmol), and HOBt.H2O (613 mg, 4.0 mmol). After stirring for 8 hours, DMF was removed by evaporation, the residue was dissolved in ethyl acetate, and then successively washed with an aqueous 10% citric acid solution, an aqueous 4% sodium bicarbonate solution, and saturated saline. After drying over MgSO4 and concentrating, the resulting oily substance was purified by flash silica gel chromatography (4×30 cm, 1% methanol/chloroform). to obtain the oily title compound (1.63 g, 3.38 mmol, 85% yield). TLC: Rf=(CHCl3/MeOH=9/1)

Workup

  1. customDMF was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washsuccessively washed with an aqueous 10% citric acid solution
  4. dry with materialAfter drying over MgSO4
  5. concentrationconcentrating
  6. customthe resulting oily substance was purified by flash silica gel chromatography (4×30 cm, 1% methanol/chloroform)

Sources & evidence

ORD record
ord-8c35c429e07e46e2a7437f4a929bab8d
Source dataset
uspto-grants-2009_02
Patent number
US07488712B2

Reaction notes

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