Sulfuric Acid → HCID 22808904, compound

HRID 426965Notes

Reaction equation

HRID 426965 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6].C1CCC(NC2CCCCC2)CC1.S(=O)(=O)(O)O.[F:34][C:35]1[C:40](O)=[C:39]([F:42])[C:38]([F:43])=[C:37]([F:44])[C:36]=1[F:45].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C.O1CCOCC1.CCOCC>[F:34][C:35]1[C:40]([O:6][C:5](=[O:7])[C@H:4]([CH2:3][CH2:2][CH3:1])[NH:8][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[C:39]([F:42])[C:38]([F:43])=[C:37]([F:44])[C:36]=1[F:45]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 44722322HCID 44722322, compound

Product 1

HCID 22808904HCID 22808904, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

8.0 g (20 mmoles) of BOC--Nva--OH.DCHA are added to a mixture of 60 ml of ether and 20 ml of 2 n aqueous sulfuric acid, and the mixture is shaken until dissolution is complete. The etheral solution is separated, washed with 20 ml of 2 n aqueous sulfuric acid and water, dried, and evaporated in vacuo. The oily residue and 3.70 g (20 mmoles) of pentafluorophenol are dissolved in 25 ml of ethyl acetate, the solution is cooled to 0° C., 3.92 g (19 mmoles) of DCC are added, and the reaction is conducted for one hour. Thereafter the suspension is filtered, the filtrate is evaporated in vacuo, and the oily residue is dissolved in 50 ml of n-hexane. The solution is washed with 5×20 ml of 5% aqueous sodium bicarbonate solution and 2×20 ml of water and evaporated in vacuo. The oily residue solidified upon cooling. 6.21 g (81%) of BOC--Nva--OPFP are obtained; m.p.: 60°-62° C., Rf3 =0.70, [α]D :-32.3° C. (c=1.0, in dioxane).

Workup

  1. customThe etheral solution is separated
  2. washwashed with 20 ml of 2 n aqueous sulfuric acid and water
  3. customdried
  4. customevaporated in vacuo
  5. filtrationThereafter the suspension is filtered
  6. customthe filtrate is evaporated in vacuo
  7. dissolutionthe oily residue is dissolved in 50 ml of n-hexane
  8. washThe solution is washed with 5×20 ml of 5% aqueous sodium bicarbonate solution and 2×20 ml of water
  9. customevaporated in vacuo
  10. temperatureupon cooling
  11. custom6.21 g (81%) of BOC--Nva--OPFP are obtained

Sources & evidence

ORD record
ord-78da1feb95a0491c8ed76e57791e7ec1
Source dataset
uspto-grants-1979_10
Patent number
US04172130

Reaction notes

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