Water → 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1087438Notes

Reaction equation

HRID 1087438 reaction equation
N[C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6](CSC1C=C(C)N3N=CC=C3N=1)=[C:7]2[C:11]([OH:13])=[O:12].O.C(N(CC)CC)C>C(#N)C>[O:10]=[C:9]1[N:8]2[CH:3]([S:4][CH2:5][CH:6]=[C:7]2[C:11]([OH:13])=[O:12])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 67821284(6R,7R)-7-amino-3-[[(7-methylpyrazolo-[1,5-a]pyrimidin-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 190919938-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.00 g of (6R,7R)-7-amino-3-[[(7-methylpyrazolo-[1,5-a]pyrimidin -5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was brought into solution in 5 ml of acetonitrile and 5 ml of water with 0.37 ml of triethylamine. The solution was treated with 1.0 g of 2-amino-4-thiazolethioglyoxylic acid S-(2-benzothiazolyl) ester and stirred at 20° for 1 hour. The reaction mixture was partitioned between water and ethyl acetate and the aqueous phase was chromatographed on Optiup (C12) (Antec AG, CH-Bennwil) with a gradient of 0% to 10% acetonitrile in water. The product fractions Were concentrated to 10 ml and adjusted to pH 2.2 with HCl. The precipitate was filtered off under suction. There was obtained (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[7-methylpyrazolo[1,5-a]pyrimidin-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[ 4.2.0]oct-2-ene-2-carboxylic acid as a yellow powder.

Workup

  1. additionThe solution was treated with 1.0 g of 2-amino-4-thiazolethioglyoxylic acid S-(2-benzothiazolyl) ester
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customthe aqueous phase was chromatographed on Optiup (C12) (Antec AG, CH-Bennwil) with a gradient of 0% to 10% acetonitrile in water
  4. concentrationThe product fractions Were concentrated to 10 ml
  5. filtrationThe precipitate was filtered off under suction

Sources & evidence

ORD record
ord-3d88bc3b639844edacc50d69f301b3bd
Source dataset
uspto-grants-1991_07
Patent number
US05036064

Reaction notes

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