Dicyclohexylcarbodiimide → HCID 178525784, compound

HRID 1502519Notes

Reaction equation

HRID 1502519 reaction equation
[C:1]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].NCCCC[OH:30].[OH:31]N1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:1]([N-:18][OH:30])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[NH:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[C:20]([OH:21])=[O:31]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 258684-Amino-1-butanolHCID 757711-HydroxybenzotriazoleHCID 688635Fmoc-L-Prolinol2×

Product 1

HCID 178525784HCID 178525784, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Compound 2 (Fmoc-L-proline) in Scheme 3 was used as a starting material. Compound 2 (10.00 g, 29.64 mmol), 4-amino-1-butanol (3.18 g, 35.56 mmol), and 1-hydroxybenzotriazole (10.90 g, 70.72 mmol) were mixed together. The mixture was deaerated under reduced pressure and filled with argon gas. Anhydrous acetonitrile (140 ml) was added to the mixture at room temperature, and an anhydrous acetonitrile solution (70 ml) of dicyclohexylcarbodiimide (7.34 g, 35.56 mmol) was further added thereto. Thereafter, this was stirred for 15 hours at room temperature in an argon atmosphere. After the completion of the reaction, the generated precipitate was removed by filtration, and the solvent in the collected filtrate was removed by evaporation under reduced pressure. Dichloromethane (200 ml) was added to the residual substance obtained, and the mixture was washed with saturated sodium bicarbonate water (200 ml). Then, an organic layer was collected and dried with magnesium sulfate. Thereafter, the organic layer was filtered, and the solvent in the filtrate obtained was removed by evaporation under reduced pressure. Diethyl ether (200 ml) was added to the residual substance, thereby turning the residual substance to powder. The thus-obtained powder was collected by filtration. Thus, Compound 4 in the form of colorless powder was obtained (10.34 g, yield: 84%). The result of NMR analysis with respect to this compound is shown below.

Workup

  1. additionfilled with argon gas
  2. customAfter the completion of the reaction
  3. customthe generated precipitate was removed by filtration
  4. customthe solvent in the collected filtrate was removed by evaporation under reduced pressure
  5. additionDichloromethane (200 ml) was added to the residual substance
  6. customobtained
  7. washthe mixture was washed with saturated sodium bicarbonate water (200 ml)
  8. customThen, an organic layer was collected
  9. dry with materialdried with magnesium sulfate
  10. filtrationThereafter, the organic layer was filtered
  11. customthe solvent in the filtrate obtained
  12. customwas removed by evaporation under reduced pressure
  13. additionDiethyl ether (200 ml) was added to the residual substance
  14. filtrationThe thus-obtained powder was collected by filtration

Sources & evidence

ORD record
ord-8bfff7e786094a6084d6e5e6277319a3
Source dataset
uspto-grants-2015_12
Patent number
US09206422B2

Reaction notes

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