Hydrochloric Acid → HCID 86749089, compound

HRID 128503Notes

Reaction equation

HRID 128503 reaction equation
[S:1]1[CH2:5][CH2:4][S:3][C:2]1=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]([NH:9][C@@H:10]1[C:21](=[O:22])[N:12]2[CH:13]([C:18]([O-:20])=[O:19])[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12)=[O:8].[Na+].Cl>O>[S:3]1[CH2:4][CH2:5][S:1][C:2]1=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]([NH:9][C@@H:10]1[C:21](=[O:22])[N:12]2[CH:13]([C:18]([OH:20])=[O:19])[C:14]([CH3:17])([CH3:16])[S:15][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86749090HCID 86749090, compound

Product 1

HCID 86749089HCID 86749089, compoundYield 73,982.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium 6β-[(1,3-dithiolan-2-ylidene)(ethoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (46 mg, 0.1 mmol) in 1 mL of H2O was added one drop (38 mg) of cone. HCl solution at 0° C. The mixture was extracted with dichloromethane several times. The combined organic layer was washed with H2O and saturated NaCl solution, dried over Na2SO4, and concentrated under reduced pressure to give the title compound (32 g, 74% yield) as a yellow oil: 1H NMR (D2O) δ 1.40 (3H, t, J=7Hz, CH2CH3), 1.55 and 1.66 (each 3H, s, C2 -(CH3)2), 3.33 (4H, s, SCH2CH2S), 4.31-4.41 (3H, m, C3 -H and OCH2CH3), 5.57 (1H, d, J=4Hz, C5-H), 5.82 (1H, dd, J=4 and 9Hz, C6-H), 9.03 (1H, d, J=9Hz, NH).

Workup

  1. customat 0° C
  2. extractionThe mixture was extracted with dichloromethane several times
  3. washThe combined organic layer was washed with H2O and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84d9e50fa4d64588889b44e09408c682
Source dataset
uspto-grants-1995_11
Patent number
US05464616

Reaction notes

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