Triethylamine → L-Isoleucine

HRID 2293361Notes

Reaction equation

HRID 2293361 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.BrCC(=O)C(C)(C)C>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 21642BromopinacoloneHCID 86751513HCID 86751513, compound

Product 1

HCID 6306L-IsoleucineYield 127.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (69 mg, 0.21 mmol), with triethylamine (151 uL, 1.08 mmol, 5.0 eq), and 1-bromopinacolone (58 uL, 0.43 mmol, 2 eq) in THF (5 mL), provided 35 mg (39%) of L-isoleucine, N-[1-(2-tert-butyl-2-oxoethyl)-L-proline] benzylamide as a colorless oil.

Sources & evidence

ORD record
ord-b1ac08b55b3f4c26aefc886e566d44fb
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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