1,2-Dichloroethane → HCID 136381122, 화합물

HRID 53579노트

반응식

HRID 53579 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.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O.C(Cl)C[Cl:50]>>[Cl:50][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]

참가 물질

5

반응물 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, 화합물

생성물 1

HCID 136381122HCID 136381122, 화합물수율 35%

실험 절차

The procedure used for the preparation of 9a was repeated with 8b (390 mg, crude from previous reaction), Et3SiH (0.80 mL, 5.0 mmol), and trifluoroacetic acid (1.50 mL, 19.5 mmol ) in dry ClCH2CH2Cl (8 mL ) at 0° C. under nitrogen to give 9b (50.0 mg, 35% for two steps) as a white solid after chromatographic separation on RP C-18 (gradient CH3CN/H2O: 25-30%, containing 1% HOAc). mp 155° C. (dec); IR (KBr) 3600-2800 (br), 3280, 1780, 1661 cm-1 ; 1H NMR (DMSO-d6) δ3.63 (1H, d, J=18.0 Hz), 3.74 (2H, s, CH2), 3.93 (1H, d, J=18.0 Hz), 5.15 (1H, d, J=4.7 Hz), 5.70 (1H, dd, J=8.0 and 4.7 Hz), 6.88 (1H, t, J=7.7 Hz), 6.96 (1H, d, J=7.7 Hz), 7.25 (1H, t, J=7.7 Hz), 7.40 (1H, s), 7.94 (1H, d, J=7.7 Hz), 9.16 (1H, d, J=8.0 Hz, NH), 11.30 (1H, s, OH), 13.80 (1H, br s, CO2H); FDMS m/z 451 (M+, 35Cl), 452 (M+ +1, 35Cl), 453 (M+, 37Cl), 454 (M+ +1, 37Cl); Anal. Calcd for C18H14ClN3O5S2 : C, 47.84; H, 3.12; N, 9.30. Found: C, 48.12; H, 3.16; N, 9.36

출처 및 근거

ORD 기록
ord-0eeeb878638140c5af1a7eb280dbdbff
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620968

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