L-(+)-Cysteine → HCID 11258094, compound

HRID 2054604Notes

Reaction equation

HRID 2054604 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:24][C@H:25]([C:28]([OH:30])=[O:29])[CH2:26][SH:27]>C(O)C.O1CCOCC1>[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]4[NH:24][CH:25]([C:28]([OH:30])=[O:29])[CH2:26][S:27]4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 5862L-(+)-CysteineHCID 59655959HCID 59655959, compound

Product 1

HCID 11258094HCID 11258094, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4′-Indol-1-yl-biphenyl-4-carbaldehyde (500 mg, 1.68 mmol) and L-cysteine (150 mg, 1.26 mmol) in ethanol (5 mL) and dioxan (5 mL) was stirred at 50° C. for 16 hours, cooled to room temperature and concentrated in vacuo. Trituration with diethyl ether gave the title compound as a beige solid (302 mg, 45%): mp. 135-137° C. (dec). Rf 0.10 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz) δ 7.82 (4H, m, Ar—H), 7.65 (6H, m, Ar—H), 7.52 (1H, d, J=8 Hz, Ar—H), 7.10-7.24 (2H, m, Ar—H), 6.74 (1H, s, Ar—H), 5.77 and 5.58 (both 0.5H, s, H-2, 1:1 diastereomers), 4.21 and 3.92 (both 0.5H, m, H-4, 1:1 diastereomers), 3.10-3.38 (2H, m, 2×H-5); ESI-LCMS e/z calcd for C24H20N2O2S: 400.500, found 401 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-875e7a62bdec4492a1fa3c837979eced
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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