Sulfuric Acid → HCID 14189817, compound

HRID 426964Notes

Reaction equation

HRID 426964 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:6]([OH:8])=[O:7].C1CCC(NC2CCCCC2)CC1.S(=O)(=O)(O)O.[F:35][C:36]1[C:41](O)=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.O1CCOCC1.CCOCC>[F:35][C:36]1[C:41]([O:7][C:6](=[O:8])[C@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[C:40]([F:43])[C:39]([F:44])=[C:38]([F:45])[C:37]=1[F:46]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 22372373HCID 22372373, compound

Product 1

HCID 14189817HCID 14189817, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

10.0g (24.3 mmoles) of BOC--Nle--OH.DCHA are added to a mixture of 75 ml of ether and 25 ml of 2 n aqueous sulfuric acid, and the mixture is shaken until the dissolution is complete. The phases are separated, and the etheral solution is washed again with 25 ml of 2 n aqueous sulfuric acid and water. The etheral solution is evaporated in vacuo. The resulting 5.44 g of oily residue and 4.42 g (24 mmoles) of pentafluorophenol are dissolved in 30 ml of ethyl acetate, the solution is cooled to 0° C., and 4.63 g (22.5 mmoles) of dicyclohexyl carbodiimide are added. The suspension is allowed to stand at a cold place for 1 hour, thereafter it is filtered, and the filtrate is evaporated in vacuo. The residue is dissolved in 50 ml of n-hexane and the solution is washed with 5×20 ml of 5% aqueous sodium bicarbonate solution and 2×20 ml of water. The organic solution is dried and evaporated in vacuo. The oily residue solidifies upon cooling. 8.12 g (91%) of BOC--Nle--OPFP are obtained; m.p.: 55°-57° C., [α]D : -26.8° (c=1.0, in dioxane), Rf2 =0.80Rf4 =0.85.

Workup

  1. customThe phases are separated
  2. washthe etheral solution is washed again with 25 ml of 2 n aqueous sulfuric acid and water
  3. customThe etheral solution is evaporated in vacuo
  4. filtrationit is filtered
  5. customthe filtrate is evaporated in vacuo
  6. dissolutionThe residue is dissolved in 50 ml of n-hexane
  7. washthe solution is washed with 5×20 ml of 5% aqueous sodium bicarbonate solution and 2×20 ml of water
  8. customThe organic solution is dried
  9. customevaporated in vacuo
  10. temperatureupon cooling
  11. custom8.12 g (91%) of BOC--Nle--OPFP are obtained

Sources & evidence

ORD record
ord-96c505b9369549039076610352c0dc9c
Source dataset
uspto-grants-1979_10
Patent number
US04172130

Reaction notes

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