Triethylamine → L-Isoleucine

HRID 2293367Notes

Reaction equation

HRID 2293367 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.ClCC(NC1C=CC(Cl)=CC=1Cl)=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 2259982-Chloro-N-(2,4-dichlorophenyl)acetamideHCID 86751513HCID 86751513, compound

Product 1

HCID 6306L-IsoleucineYield 127.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 5, treatment of a solution of L-proline-L-isoleucine benzylamide (58 mg, 0.18 mmol), with triethylamine (130 uL, 0.93 mmol, 5.0 eq), and N-chloroacetyl-2,4-dichloroaniline (53 mg, 0.22 mmol, 1.2 eq) in THF (7 mL), provided a crude product. A portion of the product was purified by preparative TLC to provide 30 mg (32%) of L-isoleucine, N-[1-(2,4-dichlorophenylcarbamoylmethyl)-L-proline] benzylamide.

Workup

  1. customprovided a crude product
  2. customA portion of the product was purified by preparative TLC

Sources & evidence

ORD record
ord-84f34aa70e3642fa9ada3fcc49d18b40
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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