HCID 23706035, compound → HCID 131714535, compound

HRID 1906603Notes

Reaction equation

HRID 1906603 reaction equation
[Na+:1].N[C@H:3]1[C@@H:6]([CH2:7][O:8][C:9](=[O:11])[NH2:10])[N:5]([S:12]([O-:15])(=[O:14])=[O:13])[C:4]1=[O:16]>CC(C)=O.O>[Na+:1].[C:9]([O:8][CH2:7][CH:6]1[N:5]([S:12]([O-:15])(=[O:14])=[O:13])[C:4](=[O:16])[CH2:3]1)(=[O:11])[NH2:10]

Participants

3

Reactant 1

HCID 23706035HCID 23706035, compound

Product 1

HCID 131714535HCID 131714535, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

1.62 g (6.20 mmol) of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt are dissolved in 180 ml of acetone/water (2:1) and the solution is treated with 3.27 g (6.83 mmol) of (Z)-2-(2-amino-4-thiazolyl)-2-[[1-[t-butoxycarbonyl]-1-methylethoxy]imino]-acetic acid 2-benzthiazolyl thioester. The mixture is stirred at room temperature for 12 hours. A further 60 mg (0.12 mmol) of the aforementioned thioester are added thereto and the stirring is continued for a further 3 hours. Acetone is removed under reduced pressure and 50 ml of water are added thereto. The crystals obtained are filtered off and washed with water. The mother liquor is partially evaporated (37° C., 15 mmHg) and chromatographed (MCI gel, water). After lyophilization, there are obtained 2.28 g (77%) of (3S,4S)-3-[2-amino-4-thiazolyl)-2-(Z)-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino] acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt.

Workup

  1. waitthe stirring is continued for a further 3 hours
  2. customAcetone is removed under reduced pressure and 50 ml of water
  3. additionare added
  4. customThe crystals obtained
  5. filtrationare filtered off
  6. washwashed with water
  7. customThe mother liquor is partially evaporated (37° C., 15 mmHg)
  8. customchromatographed (MCI gel, water)

Sources & evidence

ORD record
ord-a173b25ec5a649db97c7759d3f66bdbb
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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