2-(Benzenesulfonyl)-3-phenyloxaziridine → (8-Cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

HRID 586548Notes

Reaction equation

HRID 586548 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C:12]1[C:23](=[O:24])[N:22]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:15]2[N:16]=[C:17]([S:20][CH3:21])[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:38])C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9](=[O:30])[NH:10][CH2:11][C:12]1[C:23](=[O:24])[N:22]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:15]2[N:16]=[C:17]([S:20]([CH3:21])=[O:38])[N:18]=[CH:19][C:14]=2[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 69208844(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester

Product 1

HCID 69206663(8-Cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl esterYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(8-Cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester (1.67 g, 3.93 mmol) and 2-benzenesulfonyl-3-phenyl-oxaziridine (1.34 g, 5.11 mmol) were dissolved in dichloromethane (20 mL) and stirred at ambient temperature for 12 hours. The reaction mixture was then purified by silica gel chromatography to give (8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-carbamic acid benzyl ester as a white solid (0.98 g, 56.6%). 1H NMR δ (400 MHz, CDCl3) 8.89 (s, 1H), 7.68 (s, 1H), 7.32 (m, 5H), 5.96 (m, 1H), 5.52 (t, J=6.4 Hz, 1H), 5.09 (s, 2H), 4.32 (d, J=6.3 Hz, 2H), 2.95 (s, 3H), 2.22 (m, 2H), 2.12 (m, 2H), 1.95 (m, 2H), 1.69 (m, 2H).

Workup

  1. customThe reaction mixture was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-39c24c71fb3c4e1fa1e606ca74fd8393
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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