4-Methylmorpholine → N-(Benzenesulfonyl)-(L)-prolyl-2(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester

HRID 1596605Notes

Reaction equation

HRID 1596605 reaction equation
Cl.[NH2:2][C@@H:3]([C@@H:8]([C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)[CH3:9])[C:4]([O:6][CH3:7])=[O:5].[C:17]1([S:23]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28](O)=[O:29])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>>[C:17]1([S:23]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28]([C@@:3]([NH2:2])([C@@H:8]([C:10]2[CH:11]=[CH:12][C:13]([I:16])=[CH:14][CH:15]=2)[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[O:29])(=[O:24])=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 720844(2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867574002(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester hydrochloride

Product 1

HCID 86757402N-(Benzenesulfonyl)-(L)-prolyl-2(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl esterYield 86.2%

Procedure

To an ice cooled solution of 2(S)-amino-3(R)-(4-iodophenyl)-butyric acid, methyl ester hydrochloride (116 mg, 0.34 mmol), N-(benzenesulfonyl)-(L)-proline (128 mg, 0.50 mmol), HOBt (77 mg, 0.5 mmol) and N-methylmorpholine (55 μL, 0.5 mmol) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 99 mg, 0.5 mmol). After stirring overnight, the solvents were removed by rotoevaporation, and the residue was dissolved in methylene chloride and loaded onto a flash silica gel chromatography column. The product was eluted with 10% ethyl acetate in methylene chloride to yield 163 mg (85% yield) of the title compound.

Workup

  1. customthe solvents were removed by rotoevaporation
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe product was eluted with 10% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-6729154a572541b99eb178db90fe8525
Source dataset
uspto-grants-2001_09
Patent number
US06291511B1

Reaction notes

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