Hydrochloric Acid → HCID 66910011, compound

HRID 2040601Notes

Reaction equation

HRID 2040601 reaction equation
[OH:1][CH2:2][CH:3]1[C:15]2[CH:14]=[C:13]([NH:16]C(OC(C)(C)C)=O)[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([NH:24]C(OC(C)(C)C)=O)=[CH:7][CH:8]=2.[ClH:32]>O1CCOCC1>[ClH:32].[ClH:32].[OH:1][CH2:2][CH:3]1[C:4]2[CH:5]=[C:6]([NH2:24])[CH:7]=[CH:8][C:9]=2[C:10]2[C:15]1=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66910044HCID 66910044, compound

Product 1

HCID 66910011HCID 66910011, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

9-Hydroxymethyl-2,7-di(Boc-amino)fluorene (0.39 g, 0.9 mmol) was dissolved in 1,4-dioxane. At 0° C. concentrated HCl (2.5 mL) was added and the reaction was stirred for two hours at 0° C. and for one hour at room temperature. The reaction solvents were removed at reduced pressure (45° C.). The product was dissolved in methanol and evaporated (2 times). The product was dissolved in methanol (8 mL) and precipitated by the slow addition of diethyl ether and cooling (repeat). The product was a red-orange solid (0.25 g, 91%) that showed a single spot by TLC (chloroform/methanol/acetic acid 85:15:3, ninhydrin stain). 1H-NMR (CD3OD): δ (ppm) 8.1 (d, 2H, Ar); 7.8 (s, 2H, Ar); 7.5 (d, 2H, Ar); 4.3 (t, 1H, CH); 4.0 (d, 2H, CH2)

Workup

  1. customThe reaction solvents were removed at reduced pressure (45° C.)
  2. dissolutionThe product was dissolved in methanol
  3. customevaporated (2 times)
  4. dissolutionThe product was dissolved in methanol (8 mL)
  5. customprecipitated by the slow addition of diethyl ether
  6. temperaturecooling (repeat)

Sources & evidence

ORD record
ord-5a62133b132c49a38024897f89e7a177
Source dataset
uspto-grants-2013_11
Patent number
US08580919B2

Reaction notes

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