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Trifluoroacetic acid → 7-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

HRID 53588
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HRID 53588 반응식
C(OCC1CSC2N(C(=O)C2NC(=O)CC2N=C(C3C=CC=CC=3O)SC=2)C=1C(O)=O)(=O)C.C1(C([O:47][C:48]([C:50]2[N:51]3[CH:54]([S:55][CH2:56][CH:57]=2)[CH:53]([NH:58][C:59](=[O:73])[CH2:60][C:61]2[N:62]=[C:63]([C:66]4[CH:71]=[CH:70][CH:69]=[C:68]([OH:72])[CH:67]=4)[S:64][CH:65]=2)[C:52]3=[O:74])=[O:49])C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:72][C:68]1[CH:67]=[C:66]([C:63]2[S:64][CH:65]=[C:61]([CH2:60][C:59]([NH:58][CH:53]3[C:52](=[O:74])[N:51]4[CH:54]3[S:55][CH2:56][CH:57]=[C:50]4[C:48]([OH:49])=[O:47])=[O:73])[N:62]=2)[CH:71]=[CH:70][CH:69]=1
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6

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 731922347-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl EsterHCID 136381123HCID 136381123, 화합물

생성물 1

HCID 731922377-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
수율 99.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

The procedure used for the preparation of 9a was repeated with 8n (152 mg, 0.261 mmol), Et3SiH (0.417 mL, 2.61 mmol), and trifluoroacetic acid (0.804 mL, 10.4 mmol) in dry ClCH2CH2Cl (4 mL) at 0° C. under nitrogen to give 9n (108 mg, 99%) as a white solid after crystallization from THF/Et2O/hexane. mp 195° C. (dec); IR (KBr) 3600-2600 (br), 3343, 1787, 1682, 1532 cm-1 ; 1H NMR (DMSO-d6) δ3.49 (1H, dd, J=19.0 and 6.0 Hz), 3.59 (1H, dd, J=19.0 and 2.6 Hz ), 3.73 (2H, s, CH2), 5.01 (1H, d, J=4.9 Hz), 5.73 (1H, dd, J=8.3 and 4.9 Hz), 6.45 (1H, dd, J=6.0 and 2.6 Hz), 6.88 (1H, d, J=7.8 Hz), 7.22 (1H, t, J=7.8 Hz), 7.28 (1H, d, J=7.8 Hz), 7.29 (1H, s), 7.38 (1H, s), 9.05 (1H, d, J=8.3 Hz, NH), 9.68 (1H, s, OH), 13.15 (1H, br s, CO2H); FDMS m/z 417 (M+), 418 (M+ +1); Anal. Calcd for C18H15N3O5S2 : C, 51.79; H, 3.62; N, 10.07. Found: C, 51.95; H, 3.66; N, 9.80

출처 및 근거

ORD 기록
ord-e1463ba6939b4679b596bdbe14071bd5
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05620968

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