Triethylamine → L-Isoleucine

HRID 2293372Notes

Reaction equation

HRID 2293372 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH2:9](NC(=O)[C@H]([C@H](CC)C)N)C1C=CC=CC=1.C(N(CC)CC)C.ClCC(C1CCC(CCCCC)CC1)=O.C([C@H]1CC[C@H](C(O)=O)CC1)CCCC>C1COCC1>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[C@H:6]([CH2:7][CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21475927HCID 21475927, compoundHCID 86751513HCID 86751513, compoundHCID 178444557HCID 178444557, compound

Product 1

HCID 6306L-IsoleucineYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (160 mg, 0.50 mmol), and triethylamine (352 uL, 2.53 mmol, 5.0 eq), in THF (2 mL), was treated with 232 mg (1.0 mmol) of 1-chloro-2-(4-pentylcyclohexyl)-2-oxoethane (prepared from trans-4-pentylcyclohexanecarboxylic acid using the procedure described in example 1) to provide 154 mg, (25%) of L-isoleucine, N-[1-(2-(4-pentylycyclohexyl)-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-418d8366bb2f48cda371486bea62d194
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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