Dicyclohexylcarbodiimide → HCID 70048091, compound

HRID 1086278Notes

Reaction equation

HRID 1086278 reaction equation
[CH:1]1([CH2:10][C:11]([N:13]2[CH2:20][CH2:19][CH2:18][C@H:14]2[C:15]([OH:17])=[O:16])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[CH:1]1([CH2:10][C:11]([N:13]2[CH2:20][CH2:19][CH2:18][C@H:14]2[C:15]([O:17][CH:24]2[CH2:25][C:26](=[O:27])[NH:22][C:23]2=[O:28])=[O:16])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 70050653HCID 70050653, compound

Product 1

HCID 70048091HCID 70048091, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 4 ml of tetrahydrofuran were dissolved 0.82 g of 1-(2-indanylacetyl)-L-proline and 0.35 g of N-hydroxysuccinimide. To the solution was dropwise added a solution of 0.74 g of DCC in 2 ml of tetrahydrofuran at room temperature with stirring. After stirring for a further 17 hours at the same temperature, insoluble components were removed by filtration. From the filtrate the solvent was evaporated under reduced pressure. The oily residue thus obtained was washed with n-hexane, dissolved in 5 ml of benzene, and treated with activated carbon. Benzene was evaporated under reduced pressure to produce 0.72 g of 1-(2-indanylacetyl)-L-prolyloxysuccinimide as coloress amorphous solid.

Workup

  1. stirringAfter stirring for a further 17 hours at the same temperature, insoluble components
  2. customwere removed by filtration
  3. customFrom the filtrate the solvent was evaporated under reduced pressure
  4. customThe oily residue thus obtained
  5. washwas washed with n-hexane
  6. dissolutiondissolved in 5 ml of benzene
  7. additiontreated with activated carbon
  8. customBenzene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d54d18b369ca4e5bbcbdc2da3ad4028e
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

Loading…