(Diethylamino)sulfur trifluoride → HCID 86745886, compound

HRID 892719Notes

Reaction equation

HRID 892719 reaction equation
[CH2:1]([C@H:3]1[C@@H:6]([CH2:7]O)[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].C(N(S(F)(F)[F:26])CC)C>C(Cl)Cl>[CH2:1]([C@H:3]1[C@@H:6]([CH2:7][F:26])[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 123472(Diethylamino)sulfur trifluorideHCID 67940826HCID 67940826, compound

Product 1

HCID 86745886HCID 86745886, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (±)-cis-3-Ethyl-4-hydroxymethyl-N-toluenesulfonyl-2-azetidinone (3.9 mg) in CH2Cl2 (0.5 ml) was added diethylaminosulfur trifluoride (DAST) (15μl). The mixture was stirred overnight under nitrogen. The mixture was purified by preparative TLC on a silica gel plate (1000μ) and developed with CH2Cl2 to give the titled compound. NMR(CDCl3): δ1.06(3H, t), 1.6-2.0(2H, m), 2.45(3H, s), 3.26(1H, dt), 4.27(1H, dm), 4.65(1H, m), 4.88(1H, m), 7.37(2H, d), 7.88(2H, d)

Workup

  1. customThe mixture was purified by preparative TLC on a silica gel plate (1000μ)

Sources & evidence

ORD record
ord-eb86289616664d44afa6c04ca77bb8af
Source dataset
uspto-grants-1992_06
Patent number
US05120729

Reaction notes

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