Phenacyl bromide → L-Isoleucine

HRID 2293355Notes

Reaction equation

HRID 2293355 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.C1C[C@@H](C(O)=O)NCC1.C(=O)([O-])[O-].[Na+].[Na+].BrCC(C1C=CC=CC=1)=O>CO>[NH2:4][C@H:5]([C:7]([OH:9])=[O:8])[C@H:6]([CH2:1][CH3:2])[CH3:10]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 439227Pipecolic acid, (-)-HCID 131720272HCID 131720272, compound

Product 1

HCID 6306L-IsoleucineYield 152.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the procedure described in example 5, 55 mg (0.17 mmol) of L-homoproline-L-isoleucine benzylamide (prepared from L-homoproline (Bachem Bioscience, Philadelphia, Pa.) using the procedure described in examples 3, and 4), was treated with sodium carbonate (39 mg, 0.37 mmol), and 2-bromoacetophenone (59 mg, 0.29 mmol, 1.7 eq) in methanol (5 mL). A sample of the crude mixture was purified by preparative TLC to provide 34 mg (45%) of L-isoleucine, N-[1-(2-phenyl-2-oxoethyl)-L-homoproline] benzylamide.

Workup

  1. customA sample of the crude mixture was purified by preparative TLC

Sources & evidence

ORD record
ord-4c2bd02f41784c0fbe65986f49dfce98
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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