Sodium triacetoxyborohydride → HCID 67126820, compound

HRID 1036011Notes

Reaction equation

HRID 1036011 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:3][CH2:2]1.[O:22]1[CH2:25][C:24](=O)[CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([N:4]([CH:24]2[CH2:25][O:22][CH2:23]2)[CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 43599637HCID 43599637, compound

Product 1

HCID 67126820HCID 67126820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 308A (314 mg) in dichloromethane (5 mL) was added oxetan-3-one (72 mg) followed by sodium triacetoxyborohydride (318 mg). The mixture was stirred overnight. The mixture was diluted with dichloromethane (300 mL) and washed with aqueous NaHCO3, water and brine and dried over Na2SO4. After filtration, evaporation of the solvent gave the crude title compound.

Workup

  1. washwashed with aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration, evaporation of the solvent

Sources & evidence

ORD record
ord-194902af89a04d3a913ad46099f9aa0a
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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