Trifluoroacetic acid → HCID 23573494, compound

HRID 1825047Notes

Reaction equation

HRID 1825047 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C@H:15]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[C@H:16]([OH:19])[CH2:17][OH:18])(C)(C)C>C(Cl)Cl>[NH2:14][C@H:15]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)[C@H:16]([OH:19])[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58633294HCID 58633294, compound

Product 1

HCID 23573494HCID 23573494, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of TFA (5 mL) and (1R,2S)-(2,3-dihydroxy-1-naphthalen-2-yl-propyl)-carbamic acid tert-butyl ester (1.72 g) in methylene chloride (15 mL) was stirred for 2 h. After concentration, the residue was neutralized with 10 N NaOH and extracted with methylene chloride. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound as a solid (1.1 g).

Workup

  1. concentrationAfter concentration
  2. extractionextracted with methylene chloride
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a5d91aa27394e819339000a6038b443
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

Loading…