Hydrogen Bromide → HCID 18000963, compound

HRID 635991Notes

Reaction equation

HRID 635991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][N:15](C(O[C@@H]4C[C@H](C)CC[C@H]4C(C)(C4C=CC=CC=4)C)=O)[CH2:14][C:13]=3[NH:12][C:11]3[CH2:39][CH2:40][C:41](=[O:42])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].Br.[OH-].[NH4+]>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][NH:15][CH2:14][C:13]=3[NH:12][C:11]3[CH2:39][CH2:40][C:41](=[O:42])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 69302781HCID 69302781, compound

Product 1

HCID 18000963HCID 18000963, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product from Example 38B (0.2 g, 0.33 mmol) was treated with 48% hydrogen bromide in acetic acid (4 mL), stirred for 72 hours, neutralized with concentrated ammonium hydroxide, and extracted with methylene chloride (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated. Purification of the residue on silica gel (10% ethanol/ammonia saturated methylene chloride) to provide the title compound (0.03 g) which was converted to the HCl salt.

Workup

  1. extractionextracted with methylene chloride (3×)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue on silica gel (10% ethanol/ammonia saturated methylene chloride)

Sources & evidence

ORD record
ord-40e8a404245042f3af0b84e5334bb545
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

Loading…