Hydrogen Peroxide → HCID 90301317, compound

HRID 627662Notes

Reaction equation

HRID 627662 reaction equation
[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:16]([CH3:37])([CH3:36])[S:17](=[O:35])(=[O:34])[CH2:18][C@:19]([C:22]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=2[CH2:31][CH:32]=[CH2:33])([CH3:21])[N:20]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[OH:39]O.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:16]([CH3:37])([CH3:36])[S:17](=[O:35])(=[O:34])[CH2:18][C@:19]([C:22]2[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=2[CH2:31][CH2:32][CH2:33][OH:39])([CH3:21])[N:20]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86728130HCID 86728130, compound

Product 1

HCID 90301317HCID 90301317, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (R)-tert-butyl-N-(5-(2-allyl-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (623 mg, 1.129 mmol), in THF (11 ml) was cooled to 0° C. and borane tetrahydrofuran complex, 1.0 M in THF (1.13 ml, 1.13 mmol) was added dropwise. The mixture was stirred for 1.5 h at 0° C., then quenched with water (1 ml) and allowed to warm up to rt. The mixture was recooled to 0° C. and hydrogen peroxide (30% solution) (1.15 ml, 11.29 mmol) and sodium hydroxide (2N solution) (1.129 ml, 2.259 mmol) then were added and stirred at rt for 30 min. The mixture was partitioned between EtOAc (20 ml) and water (10 ml), organic layer was washed with brine and concentrated. The residue was purified by FC on 12 g RediSep Gold column using 20-100% EtOAc in heptane to afford (R)-tert-butyl-N-(5-(2-(3-hydroxypropyl)-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (385 mg, 0.676 mmol, 60% yield). LC/MS (ESI+) m/z=592 (M+Na).

Workup

  1. customquenched with water (1 ml)
  2. temperatureto warm up to rt
  3. customwas recooled to 0° C.
  4. stirringstirred at rt for 30 min
  5. customThe mixture was partitioned between EtOAc (20 ml) and water (10 ml), organic layer
  6. washwas washed with brine
  7. concentrationconcentrated
  8. customThe residue was purified by FC on 12 g RediSep Gold column

Sources & evidence

ORD record
ord-89d4032812f349b9be8fb015902eb30a
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…