4-Bromophenacyl bromide → HCID 67619661, compound

HRID 2293366Notes

Reaction equation

HRID 2293366 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.[CH2:9]([NH:16][C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([Br:42])=[CH:38][CH:37]=1)=[O:35]>C1COCC1>[Br:42][C:39]1[CH:40]=[CH:41][C:36]([C:34](=[O:35])[CH2:33][N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8471TriethylamineHCID 86751513HCID 86751513, compound

Product 1

HCID 67619661HCID 67619661, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (57 mg, 0.18 mmol), with triethylamine (130 uL, 0.93 mmol, 5.0 eq), and 2,-4'-dibromoacetophenone (63 mg, 0.22 mmol, 1.2 eq) in THF (7 mL), provided a crude product. A portion of the product was purified by preparative TLC to provide 62 mg (67%) of L-isoleucine, N-[1-(2-(4-bromophenyl)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customprovided a crude product
  2. customA portion of the product was purified by preparative TLC

Sources & evidence

ORD record
ord-36304a4884b44bdba13bba98796bd7ce
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

Loading…