Pentylamine → (S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-N-pentylpropionamide

HRID 660678Notes

Reaction equation

HRID 660678 reaction equation
[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C:25](=[O:27])[N:24]([CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[S:23]3(=[O:35])=[O:34])=[C:18]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:17]=2)[C:12]([OH:14])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.[CH2:56]([NH2:61])[CH2:57][CH2:58][CH2:59][CH3:60]>C(Cl)Cl>[C:1]1([S:7]([NH:10][C@@H:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C:25](=[O:27])[N:24]([CH2:28][CH2:29][Si:30]([CH3:32])([CH3:31])[CH3:33])[S:23]3(=[O:35])=[O:34])=[C:18]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:17]=2)[C:12]([NH:61][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[O:14])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8060PentylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68838051(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid

Product 1

HCID 68842520(S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-N-pentylpropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid (70 mg, 0.108 mmol) in methylene chloride (3 mL) is added EDCl (31 mg, 0.162 mmol) and the solution is stirred at RT for 3 min. To this is added n-pentylamine (10 mg, 0.119 mmol) and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound: (M−1)−=713.

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. customThe solvent is removed under reduced pressure
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-5985a4f697604a9699cf628cc38066df
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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