Dicyclohexylcarbodiimide → HCID 131715031, compound

HRID 980441Notes

Reaction equation

HRID 980441 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].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:42]1[CH2:62][CH2:61][CH2:60][C@H:43]1[C:44]([NH:46][C@H:47]([C:56]([O:58][CH3:59])=[O:57])[CH2:48][C:49]1[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=1)=[O:45]>CN(C)C=O.C(OCC)(=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:42]1[CH2:62][CH2:61][CH2:60][C@H:43]1[C:44]([NH:46][C@H:47]([C:56]([O:58][CH3:59])=[O:57])[CH2:48][C:49]1[CH:50]=[CH:51][C:52]([OH:55])=[CH:53][CH:54]=1)=[O:45])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 54049204HCID 54049204, compound

Product 1

HCID 131715031HCID 131715031, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3.5 g of Boc-Ile (16 mmol) is reacted with 3.8 g of 1-hydroxybenzotriazole (2.4 mmol) and 3.7 g of N,N'-dicyclohexylcarbodiimide (18 mmol) for 1 hour at 0° C., and then the solution of Pro-Tyr-OMe in 15 cm3 of dimethylformamide, prepared earlier, is added. After stirring for 1 hour at 0° C. and then for 10 hours at 20° C., the precipitate of dicyclohexylurea is separated off by filtration and the filtrate is concentrated. The residue obtained is dissolved in ethyl acetate and the solution obtained is washed successively with a 1M solution of citric acid, a solution of sodium bicarbonate and a solution of sodium chloride. The organic layer is dried over sodium sulphate. After removal of the solvent, the crude product is purified by chromatography on a column of silica gel (height 45 cm, diameter 2.5 cm), by eluting with ethyl acetate and mixtures of ethyl acetate with hexane. 3.8 g of Boc-Ile-Pro-Tyr-OMe are obtained, the properties of which are as follows:

Workup

  1. additionis added
  2. waitfor 10 hours at 20° C.
  3. customthe precipitate of dicyclohexylurea is separated off by filtration
  4. concentrationthe filtrate is concentrated
  5. customThe residue obtained
  6. customthe solution obtained
  7. washis washed successively with a 1M solution of citric acid
  8. dry with materialThe organic layer is dried over sodium sulphate
  9. customAfter removal of the solvent
  10. customthe crude product is purified by chromatography on a column of silica gel (height 45 cm, diameter 2.5 cm)
  11. washby eluting with ethyl acetate and mixtures of ethyl acetate with hexane

Sources & evidence

ORD record
ord-0ab98520fdb141839873e22dc1c47a63
Source dataset
uspto-grants-1987_01
Patent number
US04637997

Reaction notes

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