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

HRID 53580노트

반응식

HRID 53580 반응식
C(OC[C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:30])[CH:10]2[NH:14][C:15](=[O:29])[CH2:16][C:17]2[N:18]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[S:20][CH:21]=2)[C:7]=1[C:31]([OH:33])=[O:32])(=O)C.C1(C(OC(C2N3C(SCC=2)C(NC(=O)CC2N=C(C4C=CC=CC=4O)SC=2)C3=O)=O)C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[S:20][CH:21]=[C:17]([CH2:16][C:15]([NH:14][CH:10]2[C:9](=[O:30])[N:8]3[CH:11]2[S:12][CH2:13][CH:6]=[C:7]3[C:31]([OH:33])=[O:32])=[O:29])[N:18]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, 화합물HCID 136381125HCID 136381125, 화합물

생성물 1

HCID 1363811247-[[[2-(2-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid수율 100%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

The procedure used for the preparation of 9a was repeated with 8c (184 mg, 0.316 mmol), Et3SiH (0.505 mL, 3.16 mmol), and trifluoroacetic acid (0.972 mL, 12.6 mmol) in dry ClCH2CH2Cl (4 mL) at 0° C. under nitrogen to give 9c (132 mg, 100%) as a white solid after crystallization from THF/Et2O/hexane. mp 185° C. (dec); IR (KBr) 3700-2800 (br), 3291, 1768, 1710, 1659, 1230 cm-1 ; 1H NMR (DMSO-d6) δ3.48 (1H, dd, J=19.0 and 6.0 Hz), 3.59 (1H, dd, J=19.0 and 2.6 Hz), 3.75 (2H, s, CH2), 5.01 (1H, d, J=4.9 Hz), 5.72 (1H, dd, J=8.2 and 4.9 Hz), 6.45 (1H, dd, J=6.0 and 2.6 Hz), 6.88 (1H, t, J=7.8 Hz), 6.96 (1H, d, J=7.8 Hz), 7.25 (1H, t, J=7.8 Hz), 7.41 (1H, s), 7.94 (1H, d, J=7.8 Hz), 9.08 (1H, d, J=8.2 Hz, NH), 11.30 (1H, s, OH), 13.14 (1H, br s, CO2H); FDMS m/z 417 (M+), 418 (M+ +1); Anal. Calcd for C18H15N3O5S2. (C4H8O) 0.20: C, 52.28; H, 3.87; N, 9.73. Found: C, 52.41; H, 3.62; N, 9.71

출처 및 근거

ORD 기록
ord-b3fe743a7d15460f928ec03d6c5623d1
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620968

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