Water → HCID 20526351, compound

HRID 67936Notes

Reaction equation

HRID 67936 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][CH:8]1[CH2:14][CH:13]2[N:10]([C:11](=[O:15])[CH2:12]2)[CH:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(=[O:3])[CH3:2].[OH2:26].N1C=CC=CC=1.[Cl-:33].[Cl-].IC1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:8]1([Cl:33])[CH2:14][CH:13]2[N:10]([C:11](=[O:15])[CH2:12]2)[CH:9]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 13166207CID 13166207HCID 14890583Benzyl 3-(2-acetamidoethylthio)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 20526351HCID 20526351, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzyl 3-(2-acetamidoethylthio)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (91) (0.050 g) was dissolved in chloroform (5 ml) and stirred at 0° under argon. It was treated with water (0.010 g) and pyridine (0.022 g) followed by iodobenzene dichloride (0.038 g). A period of 2 hours was allowed to elapse and the solution was concentrated and the product chromatographed on silica gel 60 (<230 mesh) eluting with chloroform/ethanol 9:1. This gave benzyl 3-(2-acetamidoethylsulphinyl)-3-chloro-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (62) (0.040 g); m.p. 89°-93°, νmax (CHCl3) 3450, 2980, 1780, 1745, 1670 and 1515 cm-1 ; τ(CDCl3) 2.70 (5H, s, phenyl), 3.70 (1H, br, NH) 4.88 (2H, s, benzyl CH2) 4.97 (1H, s, C2-H), 5.6-5.9 (1H, m, C5-H), 6.40 (2H, q J 5 Hz, NCH2), 6.6-7.0 (4H, m, SCH2 and C6-H2), 7.05 (1H, dd J 15 and 8 Hz, C4-H), 7.68 (1H, dd J 15 and 2 Hz, C4-H) and 8.07 (3H, s, COCH3); (Found; C, 52.1; H, 5.4; N, 6.9%. C18H21ClN2O5S requires C, 52.4; H, 5.1 and N, 6.8%).

Workup

  1. customA period of 2 hours
  2. concentrationthe solution was concentrated
  3. customthe product chromatographed on silica gel 60 (<230 mesh)
  4. washeluting with chloroform/ethanol 9:1

Sources & evidence

ORD record
ord-3f5e9b4cbf7148a59197094de49cfa94
Source dataset
uspto-grants-1982_08
Patent number
US04347181

Reaction notes

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