Sodium Hydroxide → 6-{[Tetrahydro-2-thienylamino-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt

HRID 2058417

Reaction equation

HRID 2058417 reaction equation
[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:21])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].O.O.O.[S:29]1[CH2:33][CH2:32][CH2:31][CH:30]1O.[OH-].[Na+:36]>O.C(O)C>[Na+:36].[S:29]1[CH2:33][CH2:32][CH2:31][CH:30]1[NH:21][CH:13]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:11]([NH:10][CH:7]1[C:8](=[O:9])[N:4]2[CH:5]1[S:6][C:2]([CH3:25])([CH3:1])[CH:3]2[C:22]([O-:24])=[O:23])=[O:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 62883Amoxicillin TrihydrateHCID 13451042Thiolan-2-ol

Product 1

HCID 778725156-{[Tetrahydro-2-thienylamino-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of 6.7 g (0.016 mol) of amoxicillin trihydrate in 125 ml of distilled water was added in one portion 16 ml of 1 N aqueous sodium hydroxide solution. The amoxillin quickly dissolved and after two minutes 4.99 g (0.048 mol) of tetrahydrothiophene-2-ol dissolved in 10 ml of absolute ethanol was added. After stirring for two minutes at 25° C. the solution was quickly frozen and lyophilized for 19 hr to give 8.36 g of {2S-[2α, 5α, 6β(S*)]}-6-{[tetrahydro-2-thienylamino-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt as a slightly yellow pungent smelling powder.

Workup

  1. additionwas added
  2. temperaturewas quickly frozen
  3. waitlyophilized for 19 hr

Sources & evidence

ORD record
ord-ba7bcb74f88e4f67975f31e2c01413ad
Source dataset
uspto-grants-1982_03
Patent number
US04317775

Linked notes

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