Triethylamine → (6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 247029Notes

Reaction equation

HRID 247029 reaction equation
[NH2:1][CH:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[NH2:12])[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[CH3:26][O:27]/[N:28]=[C:29](/[C:33]1[N:34]=[CH:35][S:36][CH:37]=1)\[C:30](O)=[O:31]>O.O1CCCC1>[CH3:26][O:27]/[N:28]=[C:29](/[C:33]1[N:34]=[CH:35][S:36][CH:37]=1)\[C:30]([NH:1][CH:2]1[C:17](=[O:18])[N:4]2[C:5]([C:14]([OH:16])=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[NH2:12])[CH2:7][S:8][C@H:3]12)=[O:31]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 127847593-Carbamoyloxymethyl-7-amino-3-cephem-4-carboxylic acidHCID 13560156(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetic acid

Product 1

HCID 88637960(6R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-methoxyimino-2-(1,3-thiazol-4-yl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

On the other hand, 7-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (1.365 g) was suspended in a mixture of water (10 ml) and tetrahydrofuran (15 ml). While cooling with ice, triethylamine (1.01 g) was added to form a solution. To this ice-cooled solution was added dropwise the above active solution of (Z)-2-methoxyimino-2-(thiazol-4-yl)acetic acid over one hour. During the time triethylamine (total 0.78 g) was added in parts at suitable times to keep the reaction mixture at pH 6-7. After completion of the dropping, the mixture was stirred for 45 min under cooling with ice. Then the temperature was raised gradually to 15° C. After the mixture was stirred for 20 minutes at that temperature, the tetrahydrofuran was evaporated under reduced pressure. Then the aqueous layer was adjusted to pH 2-3 with 2N-HCl. The precipitates were filtered, washed with water, and dried in vacuo over phosphorus pentoxide to give the title compound (0.90 g). Further, ethyl acetate (20 ml) was added to the filtrate and the mixture was shaked. The insoluble matter formed on the interface between the aqueous layer and the ethyl acetate layer was filtered, and dried in vacuo over phosphorus pentoxide to give the title compound (0.61 g).

Workup

  1. additionwas added
  2. customto form a solution
  3. temperatureunder cooling with ice
  4. stirringAfter the mixture was stirred for 20 minutes at that temperature
  5. customthe tetrahydrofuran was evaporated under reduced pressure
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-8980bd3d53da499e95e177a5661b9126
Source dataset
uspto-grants-1987_11
Patent number
US04705784

Reaction notes

Loading…