Trifluoroacetic acid → HCID 21439015, compound

HRID 839098Notes

Reaction equation

[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:16][S:15][CH:14]3[N:11]([C:12](=[O:17])[CH2:13]3)[C:10]=2[C:18]([O:20]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:19])=[N:5][N:4]=[N:3]1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:16][S:15][CH:14]3[N:11]([C:12](=[O:17])[CH2:13]3)[C:10]=2[C:18]([OH:20])=[O:19])=[N:5][N:4]=[N:3]1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 13060635HCID 13060635, compound

Product 1

HCID 21439015HCID 21439015, compound

Procedure

The 7β-[[DL-[[[2,4-dioxo-1-imidazolidinyl)amino]carbonyl]amino]-2-thienylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)-thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, diphenylmethyl ester obtained in Example 14 is treated with trifluoroacetic acid and anisole according to the procedure of Example 8, to obtain 7β-[[DL-[[[2,4-dioxo-1-imidazolidinyl)amino]carbonyl]amino]-2-thienylacetyl]-amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, m.p. 160°-180° (dec.). The sodium salt is obtained by treating this product with an equimolar amount of sodium bicarbonate in water, filtering and freeze drying the filtrate, m.p. 200°-220° (dec.).

Sources & evidence

ORD record: ord-d81edf88910a41628b7689cd520fe8ef
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04093801

Reaction notes

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