Trifluoroacetic acid → HCID 15058047, compound

HRID 1906600Notes

Reaction equation

HRID 1906600 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:29]/[O:30][C:31]([C:34]([O:36]C(C)(C)C)=[O:35])([CH3:33])[CH3:32])/[C:15]([NH:17][C@H:18]2[C@H:21]([CH2:22][CH3:23])[N:20]([S:24]([OH:27])(=[O:26])=[O:25])[C:19]2=[O:28])=[O:16])[N:13]=1.FC(F)(F)C(O)=O>>[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:29]/[O:30][C:31]([C:34]([OH:36])=[O:35])([CH3:32])[CH3:33])/[C:15]([NH:17][C@H:18]2[C@H:21]([CH2:22][CH3:23])[N:20]([S:24]([OH:27])(=[O:26])=[O:25])[C:19]2=[O:28])=[O:16])[N:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15058045HCID 15058045, compound

Product 1

HCID 15058047HCID 15058047, compoundYield 25.6%

Procedure

250 mg of (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]acetamido]-4-ethyl-2-oxo-1-azetidinesulphonic acid triethylamine salt are added at -10° C. to 3 ml of trifluoroacetic acid. After 20 hours at -10° C., the mixture is evaporated and the residue is purified by DCCC [droplet counter current chromatography; rising droplets in the mixture chloroform/methanol/water (7:13:8)]. 58 mg of amorphous (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-4-ethyl-2-oxo-1-azetidinesulphonic acid triethylamine salt are obtained.

Workup

  1. customthe mixture is evaporated
  2. customthe residue is purified by DCCC [

Sources & evidence

ORD record
ord-7e017489bf8348cc91b8f889647175c1
Source dataset
uspto-grants-1987_03
Patent number
US04652651

Reaction notes

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