Dicyclohexylcarbodiimide → HCID 13767641, compound

HRID 2118547Notes

Reaction equation

HRID 2118547 reaction equation
[OH:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]([O:12][N+:13]([O-:15])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[S:16]([NH:20][C@H:21]([C:29](O)=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:19])(=[O:18])=[O:17].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[S:16]([NH:20][C@H:21]([C:29]([O:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([O:12][N+:13]([O-:15])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:19])(=[O:17])=[O:18]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13210631HCID 13210631, compoundHCID 13443847HCID 13443847, compound

Product 1

HCID 13767641HCID 13767641, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

31.8 g of 3,4-dihydro-8-hydroxy-3-nitroxy-2H-1-benzopyran was dissolved in 500 ml of methylene chloride, and 36.6 g of N-mesyl-L-phenylalanine and 3.7 g of 4-dimethylaminopyridine were added. With stirring at room temperature, a solution of 40 g of dicyclohexylcarbodiimide in 130 ml of methylene chloride was added, and the mixture was stirred overnight at room temperature. The precipitate was removed from the reaction mixture by filtration. The filtrate was concentrated, and the residue was dissolved in ethyl acetate and washed successively with 5% hydrochloric acid, a 5% aqueous solution of sodium hydroxide and water. The solvent was then evaporated. The residue was dissolved in tetrahydrofuran. The insoluble materials were removed by filtration. Hexane was added, and the solution was left to stand. The precipitated crystals were collected by filtration, and recrystallized from acetone to give 12.8 g (yield 19.4%) of the desired product as colorless prisms having a melting point of 191° to 195° C. (decomp.).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe precipitate was removed from the reaction mixture by filtration
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed successively with 5% hydrochloric acid
  6. customThe solvent was then evaporated
  7. dissolutionThe residue was dissolved in tetrahydrofuran
  8. customThe insoluble materials were removed by filtration
  9. additionHexane was added
  10. waitthe solution was left
  11. filtrationThe precipitated crystals were collected by filtration
  12. customrecrystallized from acetone

Sources & evidence

ORD record
ord-225c54bf996041debadd3bb50bd2c1b0
Source dataset
uspto-grants-1987_07
Patent number
US04678803

Reaction notes

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