Dicyclohexylcarbodiimide → HCID 58726192, compound

HRID 2184655Notes

Reaction equation

HRID 2184655 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH:17]1[CH2:31][CH2:30][CH2:29][C@@H:18]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].Cl.C1C=CC2N(O)N=NC=2C=1.O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:17]1[CH2:31][CH2:30][CH2:29][C@@H:18]1[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 27960291-Hydroxybenzotriazole hydrateHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 58726192HCID 58726192, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-L-Ile-OH 1/2 H2O (1.13 g, 4.7 mmol), H-D-Pro-OBzl HCl (1.14 g, 4.7 mmol) and HOBt H2O (72 mg, 0.47 mmol) were dissolved in DMF (10 ml), and TEA (0.66 ml, 4.7 mmol) and DCC (1.16 g, 5.64 mmol) were added under ice cooling, followed by stirring overnight at room temperature. After filtering and concentrating, the reaction mixture was redissolved in ethyl acetate and washed sequentially with 10% citric acid, 4% NaHCO3 and aqueous saturated sodium chloride. After drying over anhydrous MgSO4 and concentrating, purification was effected by flash silica gel chromatography (1% MeOH/CHCl3) to yield 1.76 g (89%) of the titled compound as an oily material.

Workup

  1. filtrationAfter filtering
  2. concentrationconcentrating
  3. dissolutionthe reaction mixture was redissolved in ethyl acetate
  4. washwashed sequentially with 10% citric acid, 4% NaHCO3 and aqueous saturated sodium chloride
  5. dry with materialAfter drying over anhydrous MgSO4
  6. concentrationconcentrating
  7. custompurification

Sources & evidence

ORD record
ord-d829d332a02c4d749e37c78fd96849fa
Source dataset
uspto-grants-2002_06
Patent number
US06399568B1

Reaction notes

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