Acetic Acid → N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide

HRID 852673Notes

Reaction equation

HRID 852673 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:33])[C@@H:4]([NH:12][C:13](=[O:32])[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:17]=[C:16]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:15]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:48][CH2:49][CH2:50][C:51](=O)[CH2:52][CH2:53][CH3:54].CC(O)=O>C(Cl)Cl>[CH2:5]([C@H:4]([NH:12][C:13](=[O:32])[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:17]=[C:16]([N:26]2[CH2:30][CH2:29][CH2:28][C:27]2=[O:31])[CH:15]=1)[C@H:3]([OH:33])[CH2:2][NH:1][CH:51]([CH2:52][CH2:53][CH3:54])[CH2:50][CH2:49][CH3:48])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 312464-HeptanoneHCID 5049666Sodium triacetoxyborohydrideHCID 69357401N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide

Product 1

HCID 69356145N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamideYield 11.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide (E182) (30 mg, 0.066 mmol, 1 equiv) in (CH2Cl)2 (5 ml) were added sodium triacetoxyborohydride (20 mg, 0.094 mmol, 1.4 equiv), 4-heptanone (10 μl, 0.070 mmol, 1.1 equiv) and CH3COOH (4 μl, 0.070 mmol, 1,1 equiv). The resulting mixture was stirred at room temperature for 92 hours, diluted with CH2Cl2, washed with saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/ethyl acetate: 3/2) gave N-[(1S,2R)-1-benzyl-2-hydroxy-3-(1-propyl-butylamino)-propyl]-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide (4.2 mg, 11%) as a colourless oil. [M+H]+=552.2, RT=2.98 min

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-0bc3adc8599742329258e927c37c1bd9
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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