Triethylamine → HCID 131715078, compound

HRID 1906599Notes

Reaction equation

HRID 1906599 reaction equation
N[C@H:2]1[C@@H:5]([C:6]#[CH:7])[N:4]([S:8]([OH:11])(=[O:10])=[O:9])[C:3]1=[O:12].C(N(CC)CC)C>CC(C)=O.O>[C:6]([CH:5]1[N:4]([S:8]([OH:11])(=[O:10])=[O:9])[C:3](=[O:12])[CH2:2]1)#[CH:7]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13478223HCID 13478223, compound

Product 1

HCID 131715078HCID 131715078, compound

Reagents, catalysts & solvents 1

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

Procedure

190 mg (1 mmol) of (3S,4R)-3-amino-4-ethynyl-2-oxo-1-azetidinesulphonic acid, 526 mg (1.1 mmol) of 2-(2-amino-4-thiazolyl)-2-[[(Z)-1-(t-butoxycarbonyl)-1-methylethoxy]-imino]-acetic acid 2-benzthiazolyl thioester and 0.280 ml (2 mmol) of triethylamine are stirred at room temperature for 20 hours in 5 ml of acetone/water (4:1). Thereupon, the mixture is concentrated, the residue is taken up in 4 ml of methanol and filtered. The filtrate is chromatographed over reverse-phase silica gel using water/methanol (10:1). After lyophilization there are obtained 213 mg of (3S,4R)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-tert-butoxycarbonyl)-1-methylethoxy]imino]acetamido]-4-ethynyl-2-oxo-1-azetidinesulphonic acid as an amorphous powder.

Workup

  1. concentrationThereupon, the mixture is concentrated
  2. filtrationfiltered
  3. customThe filtrate is chromatographed over reverse-phase silica gel

Sources & evidence

ORD record
ord-514498a1747d4313a63b4db1b363e5e9
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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