Sodium Carbonate → HCID 22817343, compound

HRID 1577497Notes

Reaction equation

HRID 1577497 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C@H:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C(OC(C)(C)C)=O)=[CH:19][CH:18]=2)[C:14]([OH:16])=[O:15])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C@H:13]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[C:14]([OH:16])=[O:15])[C:10]1=[O:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 22817349HCID 22817349, compound

Product 1

HCID 22817343HCID 22817343, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 9 g (21 mmols) of (3S)-3-tert.-butoxycarbonylamino-(αR)-α-(4-tert.-butoxycarbonyloxyphenyl)-2-oxo-1-azetidineacetic acid and 2.23 g (21 mmols) of Na2CO3 in 60 ml of H2O is warmed at 60° for 2 hours (pH 9). After 2 hours it is filtered and the pH of the clear colourless solution is adjusted to 2 with 2 N HCl. The precipitate is filtered off, washed with water and ethyl acetate and recrystallised from ethyl acetate and methanol. 5.8 g (~82%) of (3S)-3-(tert.-butoxycarbonylamino)-(αR)-α-(4-hydroxyphenyl)-2-oxo-1-azetidineacetic acid are obtained. Melting point: decomposition above 201°.

Workup

  1. temperatureis warmed at 60° for 2 hours (pH 9)
  2. filtrationAfter 2 hours it is filtered
  3. filtrationThe precipitate is filtered off
  4. washwashed with water and ethyl acetate
  5. customrecrystallised from ethyl acetate and methanol

Sources & evidence

ORD record
ord-f46ba96cc15d4d408488e1ae1a3ac744
Source dataset
uspto-grants-1981_09
Patent number
US04288364

Reaction notes

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