Triphenylphosphine → 3-[4-(2,2-dimethyl-[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

HRID 1821136Notes

Reaction equation

HRID 1821136 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:32][C:33]1([CH3:41])[O:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][O:34]1.[CH3:42][C:43]1[CH:48]=[C:47]([C:49]2[N:53]=[C:52]([C:54]3[S:61][C:60]([CH3:62])=[C:59]4[C:55]=3[CH2:56][C@H:57]3[C:63]([CH3:65])([CH3:64])[C@H:58]34)[O:51][N:50]=2)[CH:46]=[C:45]([CH3:66])[C:44]=1O>C1COCC1>[CH3:32][C:33]1([CH3:41])[O:38][CH2:37][CH:36]([CH2:39][O:40][C:44]2[C:45]([CH3:66])=[CH:46][C:47]([C:49]3[N:53]=[C:52]([C:54]4[S:61][C:60]([CH3:62])=[C:59]5[C:55]=4[CH2:56][C@H:57]4[C:63]([CH3:64])([CH3:65])[C@H:58]45)[O:51][N:50]=3)=[CH:48][C:43]=2[CH3:42])[CH2:35][O:34]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 5462977Diethyl azodicarboxylateHCID 1354079142,6-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]-phenol

Product 1

HCID 689798893-[4-(2,2-dimethyl-[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]oxadiazoleYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (161 mg, 0.615 mmol) in dry THF is added DEAD (0.097 mL, 0.615 mmol). The solution is stirred at rt for 1 h before (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (90 mg, 0.615 mmol) and 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]-phenol (150 mg, 0.410 mmol) is added. Stirring is continued for 24 h. The reaction mixture is purified by prep. HPLC (Waters XTerra Prep MS C18 19×50 mm 5 μm, water (0.85% NEt2)/acetonitrile) to give 3-[4-(2,2-dimethyl-[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 (135 mg) as colourless lyophilisate; LC-MS: tR=1.29 min, [M+1]+=495.30.

Workup

  1. additionis added
  2. customThe reaction mixture is purified by prep

Sources & evidence

ORD record
ord-abdbff7080944acaa5b739f3284d85da
Source dataset
uspto-grants-2009_10
Patent number
US07605269B2

Reaction notes

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