Triethylamine → L-Isoleucine

HRID 2293368Notes

Reaction equation

HRID 2293368 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(C12CC3CC(CC(C3)C1)C2)=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 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneHCID 131720272HCID 131720272, compound

Product 1

HCID 6306L-IsoleucineYield 221.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5 and Example 17, L-homoproline-L-isoleucine benzylamide (75 mg, 0.22 mmol), was treated with triethylamine (0.15 mL, 1.12 mmol, 5 eq), 1-adamantyl bromomethyl ketone (92 mg, 0.36 mmol, 1.6 eq), and THF (10 mL), to provide 64 mg (56%) of L-isoleucine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-homoproline] benzylamide.

Sources & evidence

ORD record
ord-0c604d24cd504661a22d4c46df48077e
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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