Triethylamine → HCID 67620088, compound

HRID 2293357Notes

Reaction equation

HRID 2293357 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][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=1)=[O:35]>C1COCC1>[CH3:43][O:42][C:38]1[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][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 86751513HCID 86751513, compound

Product 1

HCID 67620088HCID 67620088, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of L-proline-L-isoleucine benzylamide (125 mg, 0.39 mmol), with triethylamine (275 uL, 1,97 mmol, 5 eq), and 2-bromo-3'-methoxyacetophenone (107 mg, 0.47 mmol, 1.2 eq) in THF (20 mL), provided 149.2 mg (81%) of L-isoleucine, N-[1-(2-(3-methoxyphenyl)-2-oxoethyl)-L-prolyl] benzylamide as a pale yellow oil.

Sources & evidence

ORD record
ord-27c25ad599344a64a6790976d86793fa
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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