Triethylamine → L-Isoleucine

HRID 2293358Notes

Reaction equation

HRID 2293358 reaction equation
[CH2:1]1[CH2:6][C@@H:5]([C:7]([OH:9])=[O:8])[NH:4]C[CH2:2]1.[CH2:10](NC(=O)[C@H]([C@H](CC)C)N)C1C=CC=CC=1.C(N(CC)CC)C.BrCC(OCC1C=CC=CC=1)=O>C1COCC1>[NH2:4][C@H:5]([C:7]([OH:9])=[O:8])[C@H:6]([CH2:1][CH3:2])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 131720272HCID 131720272, compound

Product 1

HCID 6306L-IsoleucineYield 318.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5 and Example 17, L-homoproline-L-isoleucine benzylamide (43 mg, 0.13 mmol), was treated with triethylamine (91 uL, 0.65 mmol, 1.5 eq), and benzyl 2-bromoacetate (41 uL, 0.26 mmol, 2.0 eq) in THF (2.5 mL). Purification by HPLC provided 54.3 mg of L-isoleucine, N-[1-(2-(carbobenzyloxymethylene)-2-oxoethyl)-L-homoprolyl] benzylamide.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-56756981b1fb4e889ac52de0a3e9b070
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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