Triethylamine → L-Isoleucine

HRID 2293360Notes

Reaction equation

HRID 2293360 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.BrC(C(C)(C)C)C([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 21584499Bromo-t-butylacetateHCID 86751513HCID 86751513, compound

Product 1

HCID 6306L-IsoleucineYield 254.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (66 mg, 0.21 mmol), with triethylamine (147 uL, 1.05 mmol, 5.0 eq), and alpha-bromo-tert-butylacetate (68 uL, 0.42 mmol, 2 eq) in THF (5 mL), provided 70 mg (77%) of L-isoleucine, N-[1-(2-(carbo-tert-butoxymethylene)-2-oxoethyl)-L-proline] benzylamide.

Sources & evidence

ORD record
ord-82b027cfa38f4a0093b46b13b6443453
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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