Water → Benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

HRID 27741Notes

Reaction equation

HRID 27741 reaction equation
[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][CH:11]([S:26][CH2:27][CH3:28])[CH:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:29].N1C=CC=CC=1.[Cl-:36].[Cl-].IC1C=CC=CC=1>C(Cl)(Cl)Cl>[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11]([Cl:36])([S:26]([CH2:27][CH3:28])=[O:29])[CH:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 13166207CID 13166207HCID 20526358Benzyl 6-benzyl-3-ethylthio-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 20526338Benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylateYield 56.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of benzyl 6-benzyl-3-ethylthio-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (98) (0.047 g) in chloroform (5 ml) was treated with water (0.005 g), pyridine (0.033 g) and iodobenzene dichloride (0.082 g) at 0° under argon. The solution was concentrated after 2 hours and then chromatographed on silica gel 60 (<230 mesh) eluting with ethyl acetate/60°-80° petroleum ether 7:3 to give benzyl 6-benzyl-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (79) (0.030 g); m.p. 118°-123° (ethyl acetate/60°-80° petroleum ether); νmax (CHCl3) 2980, 1775 and 1745 cm-1 ; τ(CDCl3) 2.6-2.9 (10H, m, phenyls), 4.89 (2H, s, OCH2) 4.98 (1H, s, C2-H), 5.92 (1H, ddd J 8, 3 and 2 Hz, C5-H), 6.26 (1H, ddd J 9, 6 and 3 Hz, C6-H), 6.6-7.3 (5H, m, C4-H, C8-H2, SCH2), 7.72 (1H, dd J 15 and 2 Hz, C4-H) and 8.68 (3H, t J 71/2 Hz, CH3).

Workup

  1. concentrationThe solution was concentrated after 2 hours
  2. customchromatographed on silica gel 60 (<230 mesh)
  3. washeluting with ethyl acetate/60°-80° petroleum ether 7:3

Sources & evidence

ORD record
ord-fe5f1f204e694a2b8af4d95601dfa972
Source dataset
uspto-grants-1980_09
Patent number
US04223038

Reaction notes

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