1,2-Dichloroethane → HCID 136381122, compound

HRID 53579Notes

Reaction equation

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]

Participants

Reactant 4

HCID 111,2-Dichloroethane

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 136381123HCID 136381123, compound

Product 1

HCID 136381122HCID 136381122, compoundYield 35%

Procedure

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

Sources & evidence

ORD record: ord-0eeeb878638140c5af1a7eb280dbdbff
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620968

Reaction notes

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