Chloride → HCID 69241294, compound

HRID 2242184Notes

Reaction equation

HRID 2242184 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]#[N:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[BH4-].[Na+]>CO.[Co]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 312ChlorideHCID 4311764Sodium borohydrideHCID 69241992HCID 69241992, compound

Product 1

HCID 69241294HCID 69241294, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 887MethanolSolvent

Procedure

To a mixture of Example 17C (31.1 g, 0.1 mol) and cobalt (TI) chloride (11.9 g, 0.05 mol) in methanol (300 mL) at 0° C. was added in portions sodium borohydride (15.2 g, 0.4 mol). The mixture was stirred for 1 hour at room temperature, the solvent was azeotroped off with chloroform (5×300 mL). The residue was purified by silica gel chromatography with 10% methanol/90% dichloromethane/0.2% ammonium hydroxide to provide the title compound (15 g). MS (ESI) m/e 316 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 1.39 (m, 9 H) 2.35 (m, 1 H) 2.50 (m, 1 H) 2.72 (m, 2 H) 3.00 (m, 1 H) 3.13 (m, 2 H) 3.75 (m, 2 H) 3.94 (m, 1 H) 4.57 (m, 2 H).

Workup

  1. customthe solvent was azeotroped off with chloroform (5×300 mL)
  2. customThe residue was purified by silica gel chromatography with 10% methanol/90% dichloromethane/0.2% ammonium hydroxide

Sources & evidence

ORD record
ord-ecba0772e9b445cd80fcff720425bb48
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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