m-Chloroperbenzoic acid → HCID 54588461, compound

HRID 447274Notes

Reaction equation

HRID 447274 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[O:14][C@:15]4([CH2:23][N:24]=3)[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]4)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C1COCC1>[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[O:14][C@:15]4([CH2:23][N:24]=3)[CH:20]3[CH2:19][CH2:18][N+:17]([O-:33])([CH2:22][CH2:21]3)[CH2:16]4)=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86664591HCID 86664591, compound

Product 1

HCID 54588461HCID 54588461, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)—N-(5-Phenylthiazol-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.101 g, 0.297 mmol) was dissolved in THF (15 mL) and treated with m-CPBA (0.061 g, 0.356 mmol) for 30 min. at room temperature. The reaction was concentrated in vacuo to afford the crude product. The crude product was purified by reverse phase HPLC to yield pure fractions. The fractions were concentrated via vacuo and dried in a vac. oven for 18 hours to yield (S)-2-(5-phenylthiazol-2-ylamino)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octane]1′-oxide (0.03 g, 0.082 mmol, 27.8% yield) as a white powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.86-8.12 (m, 1H), 7.64 (br. s., 2H), 7.44 (s, 3H), 4.13-4.31 (m, 3H), 3.97-4.07 (m, 1H), 3.90 (d, J=10.7 Hz, 4H), 3.54-3.74 (m, 1H), 2.28-2.42 (m, 1H), 1.95-2.24 (m, 3H). LC/MS: retention time 1.04 (M+1=357.1).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto afford the crude product
  3. customThe crude product was purified by reverse phase HPLC
  4. customto yield pure fractions
  5. concentrationThe fractions were concentrated via vacuo
  6. customdried in a vac

Sources & evidence

ORD record
ord-9e7b61aa784a4df8b52ee96fc82c9b6c
Source dataset
uspto-grants-2013_07
Patent number
US08481555B2

Reaction notes

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