Triethylamine → HCID 131720275, compound

HRID 2293374Notes

Reaction equation

HRID 2293374 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]([C:36]1([CH3:42])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:35].CC1(C(O)=O)CCCCC1>C1COCC1>[CH3:42][C:36]1([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])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 707441-Methylcyclohexanecarboxylic acidHCID 13209190HCID 13209190, compoundHCID 86751513HCID 86751513, compound

Product 1

HCID 131720275HCID 131720275, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (164 mg, 0.51 mmol), and triethylamine (355 uL, 5.0 eq) in THF (2 mL), was treated with 180 mg (2.0 eq) of 1-chloro-2-(1-methyl-cyclohexyl)-2-oxoethane (prepared from 1-methyl-1-cyclohexanecarboxylic acid using the procedure described in example 1) to provide 183 mg (93%) of L-isoleucine, N-[1-(2-(1-methyl-cyclohexyl)-2-oxoethyl)-L-prolyl] benzylamide as a colorless residue.

Sources & evidence

ORD record
ord-8d20db879b5444cfa1e281e558828120
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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