Triethylamine → L-Isoleucine

HRID 2293371Notes

Reaction equation

HRID 2293371 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[CH2:9]([NH:16]C(=O)[C@H]([C@H](CC)C)N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.Cl[CH2:33][C:34]([CH:36]1[CH2:41][CH:40]2[CH2:42][CH:38]([C:39]2([CH3:44])[CH3:43])[CH:37]1[CH3:45])=[O:35].C12CC(C1(C)C)CC(C(O)=O)C2C>C1COCC1>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[C@H:6]([CH2:7][CH3:8])[CH3:9].[CH3:45][CH:37]1[CH:36]([C:34](=[O:35])[CH2:33][N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([C:10]2([CH:11]=[CH:12][CH:13]=[CH:14][CH2:15]2)[CH2:9][NH-:16])=[O:5])[CH2:41][CH:40]2[CH2:42][CH:38]1[C:39]2([CH3:43])[CH3:44]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 53510964284-84-0HCID 214759762-Chloro-1-(2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)ethan-1-oneHCID 86751513HCID 86751513, compound

Product 2

HCID 6306L-IsoleucineYield 68%HCID 131720273HCID 131720273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, a solution of L-proline-L-isoleucine benzylamide (153 mg, 0.48 mmol) and triethylamine (337 uL, 5.0 eq), in THF (2 mL), was treated with 205 mg (0.95 mmol) of 1-chloro-2-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-2-oxoethane (prepared from (-)-3-pinanecarboxylic acid using the procedure described in example 1) to provide 164 mg, (68%) of L-isoleucine, N-[1-[(2-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-2-oxoethyl]-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-7cc020696f8d494ca4c182a8525605db
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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