Dicyclohexylcarbodiimide → HCID 131716194, compound

HRID 1638573Notes

Reaction equation

HRID 1638573 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:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 195092-PyridinemethanamineHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 131716194HCID 131716194, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir 3.15 g (13.6 mmoles) of Boc-Ile, 2.08 g (13.6 mmoles) of 1-HOBT, and 1.34 g (12.3 mmoles) of 2-(aminomethyl)pyridine in 150 ml of CH2Cl2 for 10 minutes. Add 2.81 g (13.6 mmoles) of DCC and stir at room temperature for 35 minutes, then filter off DCU. Extract the filtrate with aq. NaHCO3, filter the organic layers through Na2SO4, and concentrate. Filter off DCU again, then chromatograph the crude production silica gel, eluting with 4% MeOH-CH2Cl2, to obtain 3.94 g (100%) of product. The product, Boc-Ile-AMP, is crystallized from EtOAc-hexane to give a first crop of 2.28 g with a m.p. of 102°-103.5°. Second and third crops totalling 1.50 g are also collected. Calc. for C17H27N3O3 : C, 63.52; H, 8.47; N, 13.07. Found: C, 63.37; H, 8.55; N, 12.86.

Workup

  1. filtrationfilter off DCU
  2. extractionExtract the filtrate with aq. NaHCO3
  3. filtrationfilter the organic layers through Na2SO4
  4. concentrationconcentrate
  5. filtrationFilter off DCU again
  6. washchromatograph the crude production silica gel, eluting with 4% MeOH-CH2Cl2

Sources & evidence

ORD record
ord-201a81f425f9496c975be4e7125f9f90
Source dataset
uspto-grants-1989_11
Patent number
US04880781

Reaction notes

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