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Organic & Biomolecular Chemistry
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(t, J = 8 Hz, 1H), 3.87 (br d, J = 4 Hz, 1H), 3.70-3.80 (br m, 1H),
3.54-3.58 (m, 2H), 1.22 (t, J = 16 Hz, 12H); 13C NMR (100 MHz,
CDCl3) δ 156.1, 143.8, 141.3, 131.8, 127.7, 127.0, 125.0, 124.9,
119.9, 74.2, 66.9, 64.9, 55.9, 47.2, 45.7, 28.7, 20.3; HRMS (ESI):
m/z calcd for C24H28N2O3SNa [M+Na]+ 447.1718, found:
447.1715.
Fmoc-Cys(Trt)-ψ[CH2NCS] (2p). Oily liquid (83% yield); [α]25D (c
1.0, CHCl3) -13.9; IR (νmax cm-1): 2193, 2091, 1701; 1H NMR (400
MHz, CDCl3) δ 7.75 (t , J = 8 Hz, 2H), 7.56 (d, J = 8 Hz, 2H), 7.20-
7.41 (m, 19H), 4.59 (br s, 1H), 4.40 (d, J = 8 Hz, 2H), 4.19 (t, J =
8 Hz, 1H), 3.52 (br s, 3H), 2.46 (br s, 2H); 13C NMR (100 MHz,
CDCl3) δ 155.3, 144.1, 143.6, 141.3, 133.1, 129.4, 128.1, 128.0,
127.7, 127.0, 124.9, 120.0, 67.4, 66.7, 50.2, 47.7, 47.1, 33.2;
HRMS (ESI): m/z calcd for C38H32N2O2S2Na [M+Na]+ 635.1803,
found: 635.1807.
Cbz-phg-ψ[CH2NHCSNH]-(R)-(+)-1-phenylethylamine (3a). 1H
NMR (400 MHz, CDCl3) δ 7.17-7.34 (m, 15H), 6.60 (br s, 1H),
6.10 (br s, 1H), 5.66 (br s, 1H), 5.06 (dd, J = 16 Hz, 8 Hz, 2H),
4.72-4.76 (br m, 2H), 4.0-4.08 (br m, 1H), 3.69 (br d, J = 8 Hz,
1H), 1.46 (d, J = 8 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 181.6,
156.5, 141.9, 139.0, 136.2, 129.0, 128.5, 128.2 (2C), 128.1,
127.8, 126.4, 125.7, 67.0, 60.3, 56.0, 53.8, 29.7.
Cbz-phg-ψ[CH2NHCSNH]-(S)-(-)-1-phenylethylamine (3a*). 1H
NMR (400 MHz, CDCl3) δ 7.19-7.27 ( m, 15H), 6.57 (br s, 1H),
6.04 (br s, 1H), 5.72 (br s, 1H), 4.97 (s, 2H), 4.63 (br s, 2H),
3.82-3.86 (br m, 1H), 3.71-3.77 (br m, 1H), 1.42 (d, J = 4 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ 181.5, 156.7, 142.0, 138.8,
136.2, 129.0, 128.5, 128.1, 127.9, 127.8, 126.4, 125.8, 66.8,
55.2, 53.5, 50.4, 23.6.
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Conflicts of interest
Authors declare no conflict of interest.
Acknowledgements
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We are thankful to SERB (No.EMR/2016/002432), Govt. of
India, for the financial support. S. Durgamma is thankful to
SERB for NPDF. Indian Institute of Science (IISc), Bangalore for
HRMS analysis, and Prof. P. V. Kamath and his research
scholars, Dept. of Chemistry, Central College Campus,
Bangalore University, Bangalore for IR analysis are also
thankfully acknowledged.
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