Acetone → HCID 57551721, compound

HRID 907303Notes

Reaction equation

HRID 907303 reaction equation
[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[CH2:28][N:29]3[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:7]=2)[CH2:3][CH2:2]1.[CH3:37][C:38]([CH3:40])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[CH:17]=[C:16]4[CH2:28][N:29]3[CH2:35][CH2:34][CH2:33][N:32]([CH:38]([CH3:40])[CH3:37])[CH2:31][CH2:30]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 57551729HCID 57551729, compound

Product 1

HCID 57551721HCID 57551721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 70 (50 mg) was dissolved in dichloromethane (10 mL) and acetone (0.15 mL) added. The mixture was stirred for 2 minutes then sodium triacetoxyborohydride (109 mg) added. The mixture was stirred at room temperature for 12 hours. The volatiles were removed under reduced pressure and the residue purified by HPLC to give the title compound as a solid (33 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-ed5da7be8d1348d5b1e6acda526e687f
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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