Pentylamine → HCID 67138412, compound

HRID 1592047Notes

Reaction equation

HRID 1592047 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2N(O)N=[N:7][C:5]=2C=1.C(N)CCCC.[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:40][C:39](=[O:41])[N:38]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[S:37]2(=[O:52])=[O:51])=[CH:32][CH:31]=1)[C:26]([OH:28])=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:17]([O:21][C:22](=[O:23])[NH:24][C@H:25]([C:26](=[O:28])[NH:7][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([N:36]2[CH2:40][C:39](=[O:41])[N:38]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[S:37]2(=[O:52])=[O:51])=[CH:34][CH:35]=1)([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8060PentylamineHCID 757711-HydroxybenzotriazoleHCID 67138881HCID 67138881, compound

Product 1

HCID 67138412HCID 67138412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (27 mg, 0.175 mmol), pentyl amine (0.020 mL, 0.175 mmol) and 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (37 mg, 0.192 mmol) are added to a solution of the title A compound in Example 47, (S)-2-t-butoxycarbonylamino-3-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid (91 mg, 0.175 mmol) in CH2Cl2 (4 mL) and the reaction is stirred at RT for 2 h. The mixture is concentrated and the product is taken up in EtOAc, washed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine. The organic solution is dried over anhydrous MgSO4, filtered and concentrated to give a white solid. Chromatography on a 10 g silica gel RediSep (Isco Inc.) column with a 30 mL/min gradient elution of 30:70 (EtOAc:hexane) to 60:40 over 10 min yields ((S)-2-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-carbamic acid t-butyl ester as a white solid: [M+1]+=589.

Workup

  1. concentrationThe mixture is concentrated
  2. washwashed with 1N aqueous HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic solution is dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a white solid
  7. washChromatography on a 10 g silica gel RediSep (Isco Inc.) column with a 30 mL/min gradient elution of 30:70 (EtOAc:hexane) to 60:40 over 10 min

Sources & evidence

ORD record
ord-c720ffef69604c1bacf3d1276942f193
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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