Trifluoroacetic acid → HCID 20196965, compound

HRID 1589622Notes

Reaction equation

HRID 1589622 reaction equation
NC1SC=C(/C(=N/OC(C(OC(C)(C)C)=O)(C)C)/C(N[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)N=1.[Na].FC(F)(F)C(O)=O>>[C:17]([O:16][CH2:15][CH:14]1[N:13]([S:20]([OH:23])(=[O:22])=[O:21])[C:12](=[O:24])[CH2:11]1)(=[O:19])[NH2:18]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178451070HCID 178451070, compound

Product 1

HCID 20196965HCID 20196965, 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-azetidine-sulfonic 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-9f664ad0078346d0976058955d11432f
Source dataset
uspto-grants-1986_02
Patent number
US04572801

Reaction notes

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