Hydrogen Bromide → HCID 59736983, compound

HRID 252812Notes

Reaction equation

HRID 252812 reaction equation
C(OC(=O)[NH:7][C:8]1[C:12]([NH:13]C(OC(C)(C)C)=O)=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:10][CH:9]=1)(C)(C)C.Br.CCOCC>C(O)(=O)C>[C:21]1([C:11]2[S:10][CH:9]=[C:8]([NH2:7])[C:12]=2[NH2:13])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 21631643HCID 21631643, compound

Product 1

HCID 59736983HCID 59736983, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of compound 59 in glacial acetic acid (102 μL) was added a 30% solution of HBr in acetic acid (102 μL). The mixture was stirred for 16 h at r.t. and Et2O (10 mL) was added. The precipitate was collected by filtration and immediately dissolved in water, neutralized by addition of 2N aqueous NaOH and the precipitate was extracted with Et2O. The organic layer was dried over MgSO4 and concentrated in vacuum affording the title compound 60 (34 mg, 69% yield). This procedure is essentially as described in Brugier et al., Tetrahedron, 30: 10331-10344 (1997), which is incorporated by reference in its entirety. 1H NMR: (CDCl3) δ(ppm): 7.49 (dd, J=8.4, 1.4 Hz, 2H), 7.41 (t, J=7.6 Hz, 2H), 7.26 (dd, J=10.2, 7.2 Hz, 1H), 6.22 (s, 1H), 3.51 (bs, 4H). m/z: 191.3 (MH+).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dissolutionimmediately dissolved in water
  3. additionneutralized by addition of 2N aqueous NaOH
  4. extractionthe precipitate was extracted with Et2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-ebd2c6eeaefd45e0bd0251a0df015afe
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

Loading…