Triethylamine → HCID 131720276, compound

HRID 2293375Notes

Reaction equation

HRID 2293375 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:44])[C:35]12[CH2:42][CH:41]3[CH2:43][CH:37]([CH2:38][CH:39]1[CH2:40]3)[CH2:36]2.C1C2CC3(C(O)=O)CC1CC3C2>C1COCC1>[O:44]=[C:34]([C:35]12[CH2:42][CH:41]3[CH2:43][CH:37]([CH2:38][CH:39]1[CH2:40]3)[CH2:36]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 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acidHCID 45080934HCID 45080934, compoundHCID 86751513HCID 86751513, compound

Product 1

HCID 131720276HCID 131720276, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (167 mg, 0.52 mmol), and triethylamine (367 uL, 5.0 eq) in THF (2 mL), was treated with 209 mg (1.2 eq) of 1-chloro-2-oxo-2-tricyclo[3.3.1.0 3,7 ]non-3-yl-ethane (prepared from 3-noradamantanecarboxylic acid using the procedure described in example 1) to provide 181 mg of L-isoleucine, N-[1-(2-oxo-2-tricyclo[3.3.1.0 3,7 ]non-3-yl-ethyl)-L-prolyl] benzylamide as a colorless residue.

Sources & evidence

ORD record
ord-be711f6dad694a188dfe615f305542d1
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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