Triethylamine → HCID 131720277, compound

HRID 2293376Notes

Reaction equation

HRID 2293376 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.Cl[CH2:33][C:34](=[O:47])[CH2:35][C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][C:38]([CH3:46])([CH2:39]3)[CH2:37]1)[CH2:43]2.CC12CC3CC(CC(CC(O)=O)(C3)C1)C2>C1COCC1>[O:47]=[C:34]([CH2:35][C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][C:38]([CH3:46])([CH2:39]3)[CH2:37]1)[CH2:43]2)[CH2:33][N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([N:16]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17](=[O:24])[C@H:18]([C@H:20]([CH2:22][CH3:23])[CH3:21])[NH2:19])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85698(3-Methyladamantan-1-yl)acetic acidHCID 21800923HCID 21800923, compoundHCID 86751513HCID 86751513, compound

Product 1

HCID 131720277HCID 131720277, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (162 mg, 0.51 mmol), and triethylamine (358 uL, 5.0 eq), in THF (2 mL), was treated with 246 mg (1.0 eq) of 1-chloro-2-oxo-3-(3-methyl-adamantan-1-yl) -propane (prepared from 3-methyl-1-adamantaneacetic acid using the procedure described in example 1) to provide 210 mg (78%) of L-isoleucine, N-[1-(2-oxo-3-(3-methyl-adamantan-1-yl)-propyl)-L-prolyl] benzylamide as a colorless residue.

Sources & evidence

ORD record
ord-07686a04089e4674ba18419b6f934f19
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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