Acetone → Rac-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propane-1,2-diol

HRID 1685769Notes

Reaction equation

HRID 1685769 reaction equation
C(N(CC1SC(C(O)=[O:13])=CC=1C)CC)C.C(C1C=CC(C(NO)=N)=CC=1)C=C.C([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[N:42]=[C:41]([C:43]3[S:47][C:46]([CH2:48][N:49]([CH2:52][CH3:53])[CH2:50][CH3:51])=[C:45]([CH3:54])[CH:44]=3)[O:40][N:39]=2)=[CH:34][CH:33]=1)C=C.C[N+]1([O-])CCOCC1.[CH3:63][C:64]([CH3:66])=[O:65]>O.O=[Os](=O)(=O)=O.C(O)CCC.C(Cl)Cl>[CH2:50]([N:49]([CH2:48][C:46]1[S:47][C:43]([C:41]2[O:40][N:39]=[C:38]([C:35]3[CH:36]=[CH:37][C:32]([CH2:63][CH:64]([OH:65])[CH2:66][OH:13])=[CH:33][CH:34]=3)[N:42]=2)=[CH:44][C:45]=1[CH3:54])[CH2:52][CH3:53])[CH3:51]

Participants

10

Reactant 5

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 67265583{5-[3-(4-Allyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amineHCID 178439154HCID 178439154, compound

Product 1

HCID 67265884Rac-3-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-propane-1,2-diol

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 30318Osmium TetroxideSolvent

Procedure

{5-[3-(4-Allyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amine (625 mg) is obtained as a yellow oil starting from 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (1.50 g, 6.60 mmol) and 4-allyl-N-hydroxy-benzamidine (1.28 g, 7.26 mmol) according to Method A; LC-MS: tR=0.64 min; [M+1]+=368.20. b) To a solution of {5-[3-(4-allyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amine (550 mg, 1.50 mmol) in acetone (7.5 mL) and water (0.5 mL), OsO4 (38 mg, as a 2.5% solution in butanol) followed by N-methyl morpholine-N-oxide (243 mg, 1.80 mmol) is added. The mixture is stirred at rt for 16 h. The clear yellow solution is diluted with DCM, washed with water (3×50 mL), dried over MgSO4, filtered, concentrated and dried to give crude title compound (619 mg) as yellow oil; LC-MS: tR=0.48 min; [M+1]+=401.70; 1H NMR (CDCl3): δ1.11 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 2.63 (q, J=7.3 Hz, 4H), 2.84-2.92 (m, 2H), 3.55 (dd, J=11.0, 7.0 Hz, 1H), 3.69-3.76 (m, 4H), 3.96-4.04 (m, 1H), 7.37 (d, J=7.8 Hz, 2H), 7.66 (s, 1H), 8.08 (d, J=7.8 Hz, 2H).

Workup

  1. additionis added
  2. washwashed with water (3×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried

Sources & evidence

ORD record
ord-96ae773d1f1544818610909d4fb319fa
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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