Dichloromethane → HCID 86745885, compound

HRID 892716Notes

Reaction equation

HRID 892716 reaction equation
[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][OH:8])[N:5]([S:9]([C:12]2[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[C:4]1=[O:19])[CH3:2].[CH2:20](Cl)Cl>B(F)(F)F.CCOCC>[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][O:8][CH3:20])[N:5]([S:9]([C:12]2[C:13]([CH3:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])[C:4]1=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67940826HCID 67940826, compound

Product 1

HCID 86745885HCID 86745885, compound

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateCatalyst

Procedure

To (±)-cis-3-Ethyl-4-hydroxymethyl-N-toluensulfonyl-2-azetidinone (18 mg) in CH2Cl2 at 0° to 5° C. was added boron trifluoride etherate solution (1 drop) and then diazomethane-ether solution dropwise (4 ml). The reaction mixture was purified by preparative TLC on a silica gel plate (1500μ) and developed with CH2Cl2 to afford the titled compound. NMR(CDCl3): δ1.04(3H, t), 1.54-1.92(2H, m) 2.45(3H, s), 3.16(1H, m), 3.26(3H, s), 3.70(2H, m ), 4.18(1H, m), 7.34(2H, d), 7.88(2H, d).

Workup

  1. customThe reaction mixture was purified by preparative TLC on a silica gel plate (1500μ)

Sources & evidence

ORD record
ord-a45eae93f365427c9a0d488e48158888
Source dataset
uspto-grants-1992_06
Patent number
US05120729

Reaction notes

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