N-Boc-3-(4-cyanophenyl)oxaziridine → HCID 118236114, compound

HRID 1481281Notes

Reaction equation

HRID 1481281 reaction equation
[NH2:1][C@@H:2]1[C:19]2[CH:20]=[C:15]([CH:16]=[CH:17][N:18]=2)[C:14]2[CH:13]=[CH:12][C:11]([NH:21][C:22](=[O:25])[O:23][CH3:24])=[CH:10][C:9]=2[NH:8][C:7](=[O:26])[C@H:6]([CH3:27])[CH2:5][CH2:4][CH2:3]1.C(C1C=CC(C2O[N:37]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=CC=1)#N>ClCCl>[C:42]([O:41][C:39]([NH:37][NH:1][C@@H:2]1[C:19]2[CH:20]=[C:15]([CH:16]=[CH:17][N:18]=2)[C:14]2[CH:13]=[CH:12][C:11]([NH:21][C:22](=[O:25])[O:23][CH3:24])=[CH:10][C:9]=2[NH:8][C:7](=[O:26])[C@H:6]([CH3:27])[CH2:5][CH2:4][CH2:3]1)=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

4

Reactant 2

HCID 2725038N-Boc-3-(4-cyanophenyl)oxaziridineHCID 89955662HCID 89955662, compound

Product 1

HCID 118236114HCID 118236114, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A modified procedure described by Vidal (Chem. Eur. J., 1997, 3(10), 1691) was used. To a cooled (0° C.) pink suspension of 11A (0.060 g, 0.163 mmol) in dichloromethane (1.30 mL) was added dropwise a clear, colorless solution of tert-butyl 3-(4-cyanophenyl)-1,2-oxaziridine-2-carboxylate (0.050 g, 0.204 mmol) in dichloromethane (0.651 ml). The resulting suspension was allowed to warm to rt and stir overnight. After 24 h, the majority of the solid went into solution and the solution had become a yellow color. The reaction was concentrated. Purification by normal phase chromatography gave 11B (0.033 g, 42%) as a pale yellow solid. MS (ESI) m/z: 484.2 (M+H)+. 1H NMR (500 MHz, CD3OD) δ 8.58 (d, J=5.0 Hz, 1H), 7.57 (s, 1H), 7.51-7.46 (m, 3H), 7.35 (dd, J=5.0, 1.7 Hz, 1H), 4.29 (dd, J=8.5, 5.2 Hz, 1H), 3.78 (s, 3H), 2.57-2.48 (m, 1H), 1.92-1.80 (m, 1H), 1.73-1.59 (m, 3H), 1.41 (s, 9H), 1.23-1.11 (m, 1H), 1.02 (d, J=6.9 Hz, 3H), 0.79-0.65 (m, 1H).

Workup

  1. temperatureTo a cooled
  2. waitAfter 24 h
  3. concentrationThe reaction was concentrated
  4. customPurification by normal phase chromatography

Sources & evidence

ORD record
ord-2c8b166ceab74b32a41cbf305aa19406
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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