Triethylamine → HCID 67621263, compound

HRID 2293363Notes

Reaction equation

HRID 2293363 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]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:35]>C1COCC1>[N+:42]([C:39]1[CH:38]=[CH:37][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:41][CH:40]=1)([O-:44])=[O:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668402-Bromo-4'-nitroacetophenoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67621263HCID 67621263, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (50 mg, 0.16 mmol), with triethylamine (110 uL, 0.79 mmol, 5.0 eq), and 2-bromo-4'-nitroacetophenone (48 mg, 0.20 mmol, 1.2 eq) in THF (5 mL), provided crude material that was additionally purified by preparative TLC to provide 8.8 mg (12%) of L-isoleucine, N-[1-(2-(4-nitrophenyl)-2-oxoethyl)-L-prolyl] benzylamide.

Workup

  1. customprovided crude material that
  2. customwas additionally purified by preparative TLC

Sources & evidence

ORD record
ord-3fcc8ece790b4cffb4c612c9b64d6acc
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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