HCID 23706035, compound → HCID 131714535, compound

HRID 2290490Notes

Reaction equation

HRID 2290490 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 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 a small amount of water. The mother liquor is partially evaporated (37°, 15 mmHg) and the residue is chromatographed (MCI gel, H2O). After lyophilization, there are obtained 2.28 g (77%) of (3S,4S)-3-[2-amino-4-thiazolyl)-2-(Z)-[[1-(t-butyoxycarbonyl)-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 a small amount of water
  7. customThe mother liquor is partially evaporated (37°, 15 mmHg)
  8. customthe residue is chromatographed (MCI gel, H2O)

Sources & evidence

ORD record
ord-2a1892eafa9944d4938fa06c4d6a38f7
Source dataset
uspto-grants-1986_10
Patent number
US04617150

Reaction notes

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