Trifluoroacetic acid → HCID 67793165, compound

HRID 1034247Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67821883HCID 67821883, compound

Product 1

HCID 67793165HCID 67793165, compoundYield 41.2%

Procedure

The tert-butyl ester of example 58 (320 mg, 0.686 mmol) was dissolved trifluoroacetic acid (2 ml) and stirred for 2.5 h after which time the reaction was concentrated in vacuo. The resulting material was recrystallized from CH2Cl2 /CH3OH to give 116 mg (41%) of the title compound as a white solid. Anal. calcd. for C21H18N2O5S.1/4H2O: C,60.79; H,4.49; N,6.75. Found: C,60.94; H,4.45; N,6.71. MS calc for C21H18N2O5S 410, found 410. DSC=221.0°-224.1° C. at 109.2 J/g.

Workup

concentrationwas concentrated in vacuo
customThe resulting material was recrystallized from CH2Cl2 /CH3OH

Sources & evidence

ORD record: ord-6bb1df28fe39435fb2839acf35aad3a3
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314886

Reaction notes

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