HCID 76483165, compound → HCID 76472927, compound

HRID 2290516Notes

Reaction equation

HRID 2290516 reaction equation
C([O:3][C:4]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]2[CH:24]([C:28]([OH:30])=[O:29])[CH2:25][S:26](=[O:27])[CH:20]2[CH2:19][CH2:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C>CO.O.[OH-].[Na+]>[C:4]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]2[CH:24]([C:28]([OH:30])=[O:29])[CH2:25][S:26](=[O:27])[CH:20]2[CH2:19][CH2:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 76483165HCID 76483165, compound

Product 1

HCID 76472927HCID 76472927, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of [3R-[3α,6α(S*R*),9aα]]-6[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-1-oxo-5-oxothiazolo[3,2-a]azepine-3-carboxylic acid (0.5 mmole) in 4 ml of a methanol-water mixture (1:1), 1.5 ml of 1N NaOH can be added. The reaction mixture can be stirred overnight at room temperature and then absorbed onto a strong acid ion-exchange resin such as Dowex 50 X-2, 50-100 mesh. The column can then be first eluted with water and then with 4% pyridine-water. The appropriate fraction can be freeze-dried to give the product as a diastereomeric mixture which can be separated by reverse-phase chromatography.

Workup

  1. customabsorbed onto a strong acid ion-exchange resin such as Dowex 50 X-2, 50-100 mesh
  2. washThe column can then be first eluted with water
  3. customThe appropriate fraction can be freeze-dried
  4. customto give the product as a diastereomeric mixture which
  5. customcan be separated by reverse-phase chromatography

Sources & evidence

ORD record
ord-15c6bb44425f4247ad45eed16f6ea84f
Source dataset
uspto-grants-1986_10
Patent number
US04617301

Reaction notes

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