Triethylamine → L-Isoleucine

HRID 2293373Notes

Reaction equation

HRID 2293373 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.C1C2C(=CC=CC=2)C(C(O)=O)C(C(O)=O)C1C(O)=O>C1COCC1>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[C@H:6]([CH2:7][CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86751513HCID 86751513, compoundHCID 86751535HCID 86751535, compound

Product 1

HCID 6306L-IsoleucineYield 285.5%

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 (355 uL, 5.0 eq), THF (2 mL), was treated with 212 mg (2.0 eq) of 1-chloro-2-(1,2,3,4-tetrahydro-napththalen-2-yl)-2-oxoethane (prepared from 1,2,3,4-tetrahydro-2-napththoic acid using the procedure described in Example 1) to provide 191 mg (77%) of L-isoleucine, N-[1-(2-(1,2,3,4-tetrahydro-napththalen-2-yl)-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-0a4a6093fd17464583bbf842d408b4f0
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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