Trifluoroacetate → HCID 17964995, compound

HRID 719594Notes

Reaction equation

HRID 719594 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:25])[NH:17][C@@H:18]3[C:22](=[O:23])[CH2:21][O:20][C@@H:19]3[CH3:24])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[Na+].N(C(NCC1CCC(C(O)=O)CC1)=O)N.FC(F)(F)C([O-])=O>C(O)C.O.C(Cl)(Cl)Cl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16](=[O:25])[NH:17][CH:18]3[C:22](=[O:23])[CH2:21][O:20][CH:19]3[CH3:24])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 84468TrifluoroacetateHCID 517045Sodium AcetateHCID 10198277HCID 10198277, compoundHCID 57277593HCID 57277593, compound

Product 1

HCID 17964995HCID 17964995, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

(2R, 3S) (2-methyl-4-oxo-tetrahydrofuran-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester (6b) (354 mg, 1.05 mmol, 1 eq) was dissolved in a mixture of ethanol (9.6 mL) and water (1.4 mL) containing sodium acetate.trihydrate (218 mg, 1.6 mmol, 1.5 eq). 4-[[(hydrazinocarbonyl)amino] methyl]cyclohexanecarboxylic acid. trifluoroacetate (346 mg, 1.05 mmol, 1 eq, Murphy, A. M. et al, J. Am. Chem. Soc., 114, 3156–3157, 1992) was added and the mixture refluxed for 2 hr. Chloroform (100 mL) was added and the organics washed with dilute aqueous hydrochloric acid (0.1 M, 1×100 mL). The acidic layer was backwashed with chloroform (3×100 mL) and the combined organics washed with brine (100 mL), dried (Na2SO4) and evaporated under reduced pressure to afford linker construct (8b) as a white solid (660 mg). Analytical HPLC indicated one main peak at Rt=17.011 min, HPLC-MS (main UV peak with Rt=7.96 min, 535.3 [M+H]+. Crude (8b) was used directly for construct loading.

Workup

  1. addition, 114, 3156–3157, 1992) was added
  2. temperaturethe mixture refluxed for 2 hr
  3. washthe organics washed with dilute aqueous hydrochloric acid (0.1 M, 1×100 mL)
  4. washthe combined organics washed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto afford linker

Sources & evidence

ORD record
ord-d90879dd073b4bcab41d44ee9f2cfe7c
Source dataset
uspto-grants-2006_11
Patent number
US07132449B2

Reaction notes

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