Triethylamine → HCID 10282077, compound

HRID 985391Notes

Reaction equation

HRID 985391 reaction equation
[O:1]=[C:2]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[C:4]([NH:11][C@@H:12]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]3[C:32]([Cl:33])=[CH:31][N:30]=[CH:29][C:28]=3[Cl:34])=[CH:21][CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3]1.C(N(CC)CC)C.[Br:43]Br.CCOC(C)=O>C1COCC1>[Br:43][C:3]1[C:2](=[O:1])[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[C:4]=1[NH:11][C@@H:12]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]2[C:28]([Cl:34])=[CH:29][N:30]=[CH:31][C:32]=2[Cl:33])=[CH:21][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24408BromineHCID 11720486HCID 11720486, compound

Product 1

HCID 10282077HCID 10282077, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution containing Intermediate 4 (500 mg, 0.97 mmol) and triethylamine (2 eq, 270 μl) in THF (10 ml) at 0° was treated dropwise with a solution of bromine (1.1 eq, 170 mg) in THF (5 ml). After 20 mins the reaction was allowed to warm to room temperature prior to dilution with EtOAc (100 ml). The crude reaction mixture was washed with saturated aqueous NaHCO3 (20 ml) and brine (20 ml), dried (MgSO4) filtered and concentrated in vacuo. The residual foam was chromatographed (SiO2; EtOAc) to give the title compound as a white powder (511 mg, 0.86 mmol, 95%). δH (CDCl3, 300K) 8.48 (2H, s), 8.05 (1H, s br), 7.52 (2H, d J 8.4 Hz), 7.04 (2H, d J 8.5 Hz), 5.81 (1H, d br, J 8.3 Hz), 4.98-4.91 (1H, m), 4.21 (2H, q, J 7.1 Hz), 3.21 (2H, d J 5.3 Hz), 1.70-1.66 (4H, m), 1.53-1.44 (4H, m), 1.28 (3H, t J 7.1 Hz), 1.20-1.16 (2H, m); m/z (ES+, 70V) 597.9 and 595.0 (MH+).

Workup

  1. customThe crude reaction mixture
  2. washwas washed with saturated aqueous NaHCO3 (20 ml) and brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual foam was chromatographed (SiO2; EtOAc)

Sources & evidence

ORD record
ord-328bf9870d294f0d8837c6b0dcb13361
Source dataset
uspto-grants-2005_03
Patent number
US06872719B1

Reaction notes

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