Hydrochloric Acid → HCID 66910011, compound

HRID 1530160Notes

Reaction equation

HRID 1530160 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-36d2c34fec644ab3be943242eacb0b91
Source dataset
uspto-grants-2015_07
Patent number
US09090740B2

Reaction notes

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