Hydrochloric Acid → HCID 68539250, compound

HRID 1985072Notes

Reaction equation

HRID 1985072 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[C:35]([F:37])[CH:36]=1)[CH2:5][C@H:6]([NH:26]C(=O)OC(C)(C)C)[C@H:7]([OH:25])[CH2:8][NH:9][C:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[CH:17]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.FC(F)(F)C(O)=O.[ClH:45]>C(Cl)Cl.CCOCC>[ClH:45].[ClH:45].[NH2:26][C@@H:6]([CH2:5][C:4]1[CH:34]=[C:35]([F:37])[CH:36]=[C:2]([F:1])[CH:3]=1)[C@H:7]([OH:25])[CH2:8][NH:9][C:10]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[CH:17]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 58909344HCID 58909344, compound

Product 1

HCID 68539250HCID 68539250, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To 1.98 g (3.8 mmol) of compound 5 in 15 mL of CH2Cl2 is added 6.5 mL of trifluoroacetic acid. The mixture is stirred under a nitrogen atmosphere for 1 h and then concentrated. The resulting residue is taken up in ethyl acetate and washed twice with 10% Na2CO3 and once with 1 N NaHCO3. The organic layer is dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.6 g (quant.) of a pale yellow oil (free base of 6), which is generally carried on in the next step without characterization. The yellow oil may be dissolved in ether and treated with ethereal HCl to precipitate (dihydrochloride 6 as a white solid after trituration with ether: 1H NMR (CDCl3+CD3OD drop) δ 7.55 (s, 1 H), 7.45-7.15 (m, 3 H), 6.85 (m, 2 H), 6.75 (m, 1 H), 4.4 (d, J=9.5 Hz, 1 H), 3.82 (m, 1 H), 2.97 (m, 2 H), 2.81 (dd, J=8, 14 Hz, 1 H), 2.65 (m, 2 H), 2.5 (obscured by water) 2.26 (m, 1 H), 2.13 (m, 2 H), 1.79 (m, 2 H), 1.59 (m, 1 H), 1.45-1.25 (m, 3 H), 1.28 (d, J=7 Hz, 6 H); MS (CI) m/z 417.3 (MH+).

Workup

  1. concentrationconcentrated
  2. washwashed twice with 10% Na2CO3 and once with 1 N NaHCO3
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford 1.6 g (quant.) of a pale yellow oil (free base of 6), which
  7. customto precipitate (dihydrochloride 6 as a white solid after trituration with ether

Sources & evidence

ORD record
ord-fb07ceb89132488a844f87b6c565015c
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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