Sodium Hydroxide → 2-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxymethyl}-2-nitro-propane-1,3-diol

HRID 1821140Notes

Reaction equation

HRID 1821140 reaction equation
CC1(C)[O:7][CH2:6][C:5]([CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:24]=[C:23]([C:25]4[S:32][C:31]([CH3:33])=[C:30]5[C:26]=4[CH2:27][C@H:28]4[C:34]([CH3:36])([CH3:35])[C@H:29]45)[O:22][N:21]=3)=[CH:15][C:14]=2[CH3:37])([N+:8]([O-:10])=[O:9])[CH2:4][O:3]1.[OH-].[Na+]>C1COCC1.C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.O>[CH3:19][C:18]1[CH:17]=[C:16]([C:20]2[N:24]=[C:23]([C:25]3[S:32][C:31]([CH3:33])=[C:30]4[C:26]=3[CH2:27][C@H:28]3[C:34]([CH3:35])([CH3:36])[C@H:29]34)[O:22][N:21]=2)[CH:15]=[C:14]([CH3:37])[C:13]=1[O:12][CH2:11][C:5]([N+:8]([O-:10])=[O:9])([CH2:6][OH:7])[CH2:4][OH:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 689833493-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole

Product 1

HCID 689827482-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxymethyl}-2-nitro-propane-1,3-diolYield 98.8%

Reagents, catalysts & solvents 2

HCID 22185937THF TFA waterSolventHCID 22392675Trifluoroacetic acid waterSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole (85 mg, 0.158 mmol) in THF:TFA:water 20:4:1 (12.5 mL) is stirred at 65° C. for 4.5 h. The mixture is further diluted with TFA:water 2:1 (1.5 mL) and stirring is continued at 65° C. for 3 h. The mixture is cooled to rt, poured onto 2N aq. NaOH and extracted twice with DCM. The organic extracts are dried over MgSO4 and evaporated to give 2-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxymethyl}-2-nitro-propane-1,3-diol (78 mg) as a beige resin; LC-MS: tR=1.17 min, [M+1]+=500.89.

Workup

  1. stirringstirring
  2. waitis continued at 65° C. for 3 h
  3. temperatureThe mixture is cooled to rt
  4. extractionextracted twice with DCM
  5. dry with materialThe organic extracts are dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-47cf20a128924ae0b420e71ca5d2181c
Source dataset
uspto-grants-2009_10
Patent number
US07605269B2

Reaction notes

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