Sodium hydride → HCID 19605405, compound

HRID 1603659Notes

Reaction equation

HRID 1603659 reaction equation
[CH2:1]([S:8][CH:9]1[NH:12][C:11](=[O:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]OS(C(F)(F)F)(=O)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:12]2[CH:9]([S:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:10][C:11]2=[O:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19605253HCID 19605253, compoundHCID 19605415HCID 19605415, compound

Product 1

HCID 19605405HCID 19605405, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treatment of 4-benzylthio-2-oxo-azetidine (1.35 g) in THF with NaH (0.18 g) followed by 9-phenylnonyltriflate (2.8 g) gave the title compound as a colourless oil, 1.9 g, 68% yield. 1H NMR δ (CDCl3) 1.2-1.7 (14H, m, 7×CH2), 2.60 (2H, t, J=8 Hz, CH2Ar), 2.8, 3.2 (each 2H, m, H3 +NCH2), 3.76 (2H, s, SCH2), 4.59 (1H, m, H4), 7.15-7.35 (10H, m, Ph--H)

Sources & evidence

ORD record
ord-d8041de17066417d853a82ed724599ef
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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