Hydrogen Bromide → HCID 70160773, compound

HRID 842612Notes

Reaction equation

HRID 842612 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH2:7][C:8](=[O:29])[CH2:9][N:10]([C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])C(=O)OCC1C=CC=CC=1)([O-:3])=[O:2].[BrH:34]>O1CCOCC1.C(O)(=O)C>[BrH:34].[N+:1]([C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH2:7][C:8]([CH2:9][NH:10][C@@H:21]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:22])=[O:29])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 70159661HCID 70159661, compound

Product 1

HCID 70160773HCID 70160773, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from Example 1D (19 g, 42.4 mmol) in 1,4-dioxane (100 mL) at 10° C. was treated with 30% HBr in acetic acid (30 mL), stirred for 30 minutes, purged with nitrogen, poured into diethyl ether (600 mL), triturated, and filtered to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ1.60 (d, 3H), 3.98 (d, 1H), 4.20 (d, 1H), 4.38 (q, 1H), 5.14 (s, 2H), 7.16 (t, 1H), 7.25 (d, 1H), 7.40-7.55 (m, 5H), 7.63 (t, 1H), 7.91 (d,1H), 9.20-9.60 (bs, 2H).

Workup

  1. custompurged with nitrogen
  2. additionpoured into diethyl ether (600 mL)
  3. customtriturated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ab3173bcf629436f9e985820037ca757
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

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