Hydrochloric Acid → HCID 91156048, compound

HRID 50639

Reaction equation

HRID 50639 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O.[CH2:22]([O:24][C:25](=[O:32])[C@H:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH2:27])[CH3:23].Cl.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([NH:27][C@@H:26]([CH2:28][CH:29]([CH3:30])[CH3:31])[C:25]([O:24][CH2:22][CH3:23])=[O:32])=[O:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 75971L-Leucine ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227366192-(2-Bromophenyl)thio-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 91156048HCID 91156048, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-bromophenyl)thio-3-(4-methoxyphenyl)propanoic acid (1.102 g) and L-leucine ethyl ester.HCl (704 mg) in DMF (10 mL), HOBt (551 mg) and EDC.HCl (690 mg) were added. The reaction mixture was stirred at r.t. overnight. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with 1N HCl, 5% Na2CO3 aq. and brine. The organic layer was dried over Na2SO4 and concentrated to give the pure product as a pale yellow oil (1.561 g, quant.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 1N HCl, 5% Na2CO3 aq. and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b6ea4dc3999243a4923133973afb1594
Source dataset
uspto-grants-2004_03
Patent number
US06713477B1

Linked notes

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