Bicyclo[2.2.1]heptane-2-carboxylic acid → L-Isoleucine

HRID 2293412Notes

Reaction equation

HRID 2293412 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.C12CC(CC1)CC2C(O)=O.C([NH-])C1C=CC=CC=1>>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[C@H:6]([CH2:7][CH3:8])[CH3:9]

Participants

4

Reactant 3

HCID 79113Bicyclo[2.2.1]heptane-2-carboxylic acidHCID 22619318Benzyl amideHCID 86751513HCID 86751513, compound

Product 1

HCID 6306L-IsoleucineYield 164.4%

Procedure

Using the procedure described in Example 5, treatment of L-proline-L-isoleucine benzylamide (100 mg, 0.32 mmol) with 2-norbornyl α-chloromethyl ketone (82 mg, 0.48 mmol, 1.5 eq; prepared from 2-norbornanecarboxylic acid by the method described in Example 1) provided 69 mg of L-isoleucine, N-[1-(2-bicyclo[2.2.1]hept-2-yl)-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-96a06f3bd3434efb832c7e02aa68e3d9
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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