Trifluoroacetic acid → HCID 54104709, compound

HRID 2292340Notes

Reaction equation

[OH:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][S:13]([NH:16][C:17]([N:19]2[CH2:22][C@H:21]([NH:23]C(OCC3C=CC=CC=3)=O)[C:20]2=[O:34])=[O:18])(=[O:15])=[O:14])[CH:3]=1.C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:23][C@H:21]1[CH2:22][N:19]([C:17]([NH:16][S:13]([NH:12][C:4]2[CH:3]=[C:2]([OH:1])[C:10]([OH:11])=[CH:9][C:5]=2[C:6]([OH:8])=[O:7])(=[O:14])=[O:15])=[O:18])[C:20]1=[O:34]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7520Thioanisole

HCID 22841378HCID 22841378, compound

Product 1

HCID 54104709HCID 54104709, compoundYield 159.6%

Conditions

Temperature: 10 °C

Procedure

4 Grams (0.008 mol) of (S)-4,5-dihydroxyl-2-[[[[[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]carbonyl]amino]sulfonyl]amino]benzoic acid was added at 10° C. to a stirred mixture of 3.2 ml of thioanisole and 14 ml of trifluoroacetic acid. The mixture was stirred overnight at 10° C., evaporated and treated with ether to yield 4.6 g of crude (S)-2-[[[[(3-amino-2-oxo-1-azetidinyl)carbonyl]amino]sulfonyl]amino]-4,5-dihydroxybenzoic acid.

Workup

customevaporated
additiontreated with ether

Sources & evidence

ORD record: ord-3a42f34dec614b209a84a4adf2269300
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801705

Reaction notes

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