HCID 744894, compound → L-Lysine

HRID 397769Notes

Reaction equation

HRID 397769 reaction equation
C([N:5](S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])C(C)C.C1(S(N[C@H](C(O)=O)CC2C=CC=CC=2)(=O)=O)C=CC=CC=1>>[NH2:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11]

Participants

3

Reactant 2

HCID 744894HCID 744894, compoundHCID 69107391HCID 69107391, compound

Product 1

HCID 5962L-Lysine

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine (385 mg, 1.0 mmol, example 5, step C) as described in general procedure Bc using Nα-benzenesulfonyl-L-phenylalanine (335 mg, 1.1 mmol) which was prepared in step A of example 8. The final product was purified by preparative HPLC to yield 550 mg (85%) of Nα-(4-nitrobenzenesulfonyl)-Nα-isobutyl-Nε-(N′α-benzenesulfonyl)-L-phenylalanyl)-L-lysine. The latter derivative (200 mg) was hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (129 mg, 65%).

Workup

  1. customwas prepared in step A of example 8
  2. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7e8e885c5d0f4660ae81d005cff227e7
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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