Trifluoroacetic acid → HCID 13470809, compound

HRID 652826Notes

Reaction equation

HRID 652826 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([O:32]C(C)(C)C)=[O:31])([CH3:29])[CH3:28])/[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[N:13]([S:20]([OH:23])(=[O:22])=[O:21])[C:12]2=[O:24])=[O:9])[N:6]=1.[Na].FC(F)(F)C(O)=O>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][C:27]([C:30]([OH:32])=[O:31])([CH3:28])[CH3:29])/[C:8]([NH:10][C@H:11]2[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[NH2:18])[N:13]([S:20]([OH:23])(=[O:22])=[O:21])[C:12]2=[O:24])=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178451070HCID 178451070, compound

Product 1

HCID 13470809HCID 13470809, compound

Procedure

2.28 g of (3S,4S)-3-[(2-amino-4-thiazolyl)-2-(Z)-[[1-(t-butoxycarbonyl)-1-methylethoxy]imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulfonic acid-sodium salt are stirred at 0° C. with 5 ml of trifluoroacetic acid. After additional stirring at room temperature for 30 minutes the excess trifluoroacetic acid is removed in vacuo and the remaining oil treated with 100 ml of ether. The resulting crystals are filtered off, washed with ether and dried in vacuo. The product is purified by reverse phase chromatography and lyophilized. (3S,4S)-3-[(Z)-2-(2-Amino-4-thiazolyl)-2-[[1-carboxy-1-methylethoxy]imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulfonic acid is obtained; [α]D =+35.7° (c=0.3 in water).

Workup

  1. customis removed in vacuo
  2. additionthe remaining oil treated with 100 ml of ether
  3. filtrationThe resulting crystals are filtered off
  4. washwashed with ether
  5. customdried in vacuo
  6. customThe product is purified by reverse phase chromatography

Sources & evidence

ORD record
ord-779a2eb6e35a4ff093367316b12085fc
Source dataset
uspto-grants-1987_06
Patent number
US04673739

Reaction notes

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