Hydrochloric Acid → (2S)-6-[(2-anilinoacetyl)amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 396912Notes

Reaction equation

HRID 396912 reaction equation
[K+].[CH2:2]([N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:7]([C:13]([O-:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:3]([CH3:5])[CH3:4].CC[N:28]([CH:32]([CH3:34])C)[CH:29]([CH3:31])[CH3:30].ClCC(Cl)=[O:38].Cl.[CH2:41]1[CH2:45]OC[CH2:42]1>>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([N:6]([C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:34]([CH2:32][NH:28][C:29]2[CH:30]=[CH:45][CH:41]=[CH:42][CH:31]=2)=[O:38])[CH2:2][CH:3]([CH3:4])[CH3:5])(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 131723744Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine potassium salt

Product 1

HCID 508626(2S)-6-[(2-anilinoacetyl)amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine potassium salt (2.0 g, 5.1 mmol) suspended in a mixture of THF (20 mL), DIEA (1.5 mL, 8.6 mmol) and chloroacetyl chloride (0.8 mL, 10.1 mmol). The reaction mixture was stirred for a period of 30 min. Then, a solution of 2N HCl (20 mL) was added and the solution extracted with EtOAc (25 mL, 3×). The organic phase was dried with MgSO4, filtered and evaporated to a brown oil. The crude material was purified by flash chromatography using a solvent gradient from 39:1 to 19:1 CH2Cl2/MeOH. The product was isolated as a yellowish oil (1.7 g, 78% yield).

Workup

  1. extractionthe solution extracted with EtOAc (25 mL, 3×)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. customevaporated to a brown oil
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-195af64bd7d3495daefcbc08214139e9
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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