Sodium Hydroxide → HCID 13239640, compound

HRID 1607997Notes

Reaction equation

HRID 1607997 reaction equation
I.[NH2:2][C@@H:3]1[C:20](=[O:21])[N:5]2[C:6]([C:17]([O-:19])=[O:18])=[C:7]([CH2:10][N+:11]3([CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:8][S:9][C@H:4]12.[OH-].[Na+].C1C=CC2N(O)N=NC=2C=1.[CH3:34][O:35]/[N:36]=[C:37](\[C:44](O)=[O:45])/[C:38]1[N:42]=[C:41]([NH2:43])[S:40][CH:39]=1>O.O1CCCC1>[NH2:43][C:41]1[S:40][CH:39]=[C:38](/[C:37](=[N:36]/[O:35][CH3:34])/[C:44]([NH:2][CH:3]2[C:20](=[O:21])[N:5]3[C:6]([C:17]([O-:19])=[O:18])=[C:7]([CH2:10][N+:11]4([CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12]4)[CH2:8][S:9][C@H:4]23)=[O:45])[N:42]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide5×HCID 757711-HydroxybenzotriazoleHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 13591237111390-01-3

Product 1

HCID 13239640HCID 13239640, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A total of 12.76 g (30 mmoles) of (6R,7R)-7-amino-3-(1-methyl-1-pyrrolidinio)methylceph-3-em-4-carboxylate monohydroiodide (prepared in Example 19) was suspended in 87 ml of water with good stirring at 20°-25° C. The slurry was cooled to 8°-10° C., and the pH was raised to 5.80 at 7° C. by dropwise addition of 13.0 ml (26 mmoles, 0.87 equivalents) of 2N sodium hydroxide solution over a period of 35 minutes. Next, 555 ml of tetrahydrofuran was added, and the pH of the resulting solution was increased to 6.8 at 10° C. by dropwise addition of 1.9 ml (3.8 mmoles, 0.13 equivalents) of 2N sodium hydroxide solution. The cooling bath was removed, and 29.5 g (92.7 mmoles, 1.5 equivalents) of the HOBT active ester of syn-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid was added in two equal portions of 14.75 g each over 30 minutes. Following each addition, the pH was readjusted to 6.5 every 5-10 minutes, by dropwise addition of 2N sodium hydroxide solution. In the remaining reaction time, the pH was readjusted to 6.5 by dropwise addition of 2N sodium hydroxide solution every 15 minutes (total 2N sodium hydroxide used was 28.6 ml (57.2 mmoles, 1.91 equivalents).

Workup

  1. temperatureThe slurry was cooled to 8°-10° C.
  2. customThe cooling bath was removed
  3. additioneach addition
  4. customIn the remaining reaction time

Sources & evidence

ORD record
ord-19f0b1d7fa3e4e079d1299d5e11b0df4
Source dataset
uspto-grants-1989_09
Patent number
US04868294

Reaction notes

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