Potassium tert-butoxide → HCID 90308599, compound

HRID 627666Notes

Reaction equation

HRID 627666 reaction equation
[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:20]([CH3:22])([CH3:21])[S:19](=[O:24])(=[O:23])[C@H:18]2[CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=3[C@@:17]2([CH3:37])[N:16]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:20]([CH3:22])([CH3:21])[S:19](=[O:23])(=[O:24])[C@@H:18]2[CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=3[C@@:17]2([CH3:37])[N:16]=1)[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 90308594HCID 90308594, compound

Product 1

HCID 90308599HCID 90308599, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl-N-((4aS,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tert-butoxycarbonyl-carbamate (806 mg, 1.461 mmol) in THF (10 ml) was treated with potassium tert-butoxide (1M in THF) (0.584 ml, 0.584 mmol) dropwise at rt. The mixture became dark after first few drops added. After 5 min stirring the reaction was quenched by 3 ml sat NH4Cl solution, stirred for 5 min, then diluted with water (2 ml) and EtOAc (3 ml). Organic layer was washed with brine and concentrated. The residue was purified by FC using 40 g RediSep Gold column (10-70% EtOAc in heptane) to afford tert-butyl-N-((4aR,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tertbutoxycarbonyl-carbamate (615 mg, 1.115 mmol, 76% yield). LC/MS (ESI+) m/z=574 (M+Na).

Workup

  1. additionadded
  2. customwas quenched by 3 ml
  3. stirringstirred for 5 min
  4. additiondiluted with water (2 ml) and EtOAc (3 ml)
  5. washOrganic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was purified by FC

Sources & evidence

ORD record
ord-fdb418934c414b839a0f2fca05708b42
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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