Z.-M. Qian, K.-L. Zuo, Z. Guan et al.
Tetrahedron 83 (2021) 131999
4
(
.2.2. N-(2-hydroxy-2-phenyl-3-tosylpropyl)-N-phenylacetamide
3b)
White solid (54.6 mg, 65%), m.p. 168.5e169.2 C. 1H NMR
600 MHz, CDCl
126.3, 76.6, 64.2, 61.3, 23.0, 21.0 ppm.
ꢀ
4.2.8. N-(3-((2-chlorophenyl)sulfonyl)-2-hydroxy-2-phenylpropyl)-
N-phenylacetamide (3h)
(
(
(
1
1
3
)
d
7.47 (d, J ¼ 8.1 Hz, 2H), 7.29e7.23 (m, 3H), 7.17
White solid (54.3 mg, 61%), m.p. 168.3e169.1 C. 1H NMR
ꢀ
d, J ¼ 7.3 Hz, 2H), 7.14e7.12 (m, 3H), 7.09e7.06 (m, 2H), 6.84e6.75
m, 2H), 5.67 (brs, 1H), 4.93 (d, J ¼ 14.5 Hz, 1H), 3.96 (d, J ¼ 15.2 Hz,
(600 MHz, DMSO‑d
6
)
d
7.69 (d, J ¼ 7.8 Hz, 1H), 7.64e7.64 (m, 2H),
H), 3.74 (d, J ¼ 15.2 Hz, 1H), 3.56 (d, J ¼ 14.5 Hz, 1H), 2.38 (s, 3H),
7.46 (t, J ¼ 6.5 Hz, 1H), 7.24e7.22 (m, 5H), 7.15e7.07 (m, 3H),
6.84e6.72 (m, 2H), 5.93 (s, 1H), 4.71 (d, J ¼ 14.4 Hz, 1H), 4.24 (d,
J ¼ 15.3 Hz, 1H), 4.15 (d, J ¼ 15.1 Hz, 1H), 3.71 (d, J ¼ 14.4 Hz, 1H),
.79 (s, 3H) ppm. 13C NMR (150 MHz, DMSO‑d
43.1, 139.4, 129.6, 129.4, 129.1, 128.2, 128.0, 127.9, 127.7, 127.1, 126.3,
6.7, 64.3, 61.0, 22.9, 21.5 ppm.
6
) d 173.5, 144.7, 143.8,
1
7
13
6
1.64 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d ) d 172.9, 144.1, 142.1,
138.7,134.6,131.3, 131.0,130.7,128.9,127.5,127.4,127.2, 126.8,125.5,
4
.2.3. N-(2-hydroxy-3-((4-methoxyphenyl)sulfonyl)-2-
phenylpropyl)-N-phenylacetamide (3c)
White solid (55.5 mg, 63%), m.p. 159.4e160.3 C. 1H NMR
600 MHz, DMSO‑d
7.61 (d, J ¼ 8.6 Hz, 2H), 7.24 (d, J ¼ 7.0 Hz,
H), 7.22e7.16 (m, 3H), 7.15e7.08 (m, 3H), 6.99 (d, J ¼ 8.7 Hz, 2H),
.77e6.62 (m, 2H), 5.97 (s, 1H), 4.72 (d, J ¼ 14.4 Hz, 1H), 3.97 (d,
76.0, 62.0, 60.6, 22.4 ppm.
ꢀ
4.2.9. N-(3-((3-chlorophenyl)sulfonyl)-2-hydroxy-2-phenylpropyl)-
N-phenylacetamide (3i)
(
2
6
6
) d
White solid (52.2 mg, 59%), m.p. 143.1e143.9 C. 1H NMR
ꢀ
(600 MHz, DMSO‑d
6
)
d
7.68 (d, J ¼ 7.7 Hz, 2H), 7.64 (s, 1H), 7.53 (t,
J ¼ 15.0 Hz, 1H), 3.84 (d, J ¼ 16.7 Hz, 4H), 3.76 (d, J ¼ 14.4 Hz, 1H),
.62 (s, 3H) ppm. 13C NMR (150 MHz, DMSO‑d
173.5, 163.2, 144.7,
43.0, 133.7, 130.5, 129.4, 128.0, 127.9, 127.6, 127.2, 126.3, 114.4, 76.7,
J ¼ 7.8 Hz, 1H), 7.24 (d, J ¼ 7.2 Hz, 2H), 7.22e7.16 (m, 3H), 7.13e7.10
(m, 3H), 6.79e6.62 (m, 2H), 6.08 (s, 1H), 4.70 (d, J ¼ 14.4 Hz, 1H),
4.12 (d, J ¼ 15.2 Hz, 1H), 4.05 (d, J ¼ 15.2 Hz, 1H), 3.77 (d, J ¼ 14.4 Hz,
1
1
6
6
) d
1
3
4.5, 61.0, 56.2, 22.9 ppm. HRMS (ESI) calc. for C24
H
25NO
5
S
6
1H), 1.63 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d ) d 173.5, 144.6,
þ
(
M þ Na) : 462.1346, found: 462.1341.
144.0, 142.6, 133.7, 133.4, 131.1, 129.4, 128.1, 128.0, 127.9, 127.7, 127.3,
26.9, 126.3, 76.5, 64.1, 61.1, 22.9 ppm.
1
4.2.4. N-(3-((4-chlorophenyl)sulfonyl)-2-hydroxy-2-phenylpropyl)-
N-phenylacetamide (3d)
White solid (60.3 mg, 68%), m.p. 168.5e169.2 C. 1H NMR
600 MHz, DMSO‑d
7.69 (d, J ¼ 8.0 Hz, 2H), 7.56 (d, J ¼ 8.3 Hz,
H), 7.24e7.10 (m, 8H), 6.74e6.56 (m, 2H), 6.06 (s, 1H), 4.69 (d,
J ¼ 14.4 Hz, 1H), 4.07 (d, J ¼ 15.1 Hz, 1H), 3.97 (d, J ¼ 15.1 Hz, 1H),
4.2.10. N-(2-hydroxy-2-phenyl-3-(thiophen-2-ylsulfonyl)propyl)-
N-(4-methoxyphenyl)acetamide (3j)
ꢀ
White solid (47.2 mg, 53%), m.p. 125.6e126.5 C. 1H NMR
ꢀ
(
2
6
)
d
(600 MHz, CDCl
3
)
d
7.58 (d, J ¼ 4.6 Hz, 1H), 7.31 (d, J ¼ 3.0 Hz, 1H),
7.25e7.22 (m, 2H), 7.19e7.16 (m, 3H), 6.93e6.92 (m, 1H), 6.75e6.59
(m, 4H), 4.93 (d, J ¼ 14.4 Hz, 1H), 4.04 (d, J ¼ 15.2 Hz, 1H), 3.84 (d,
J ¼ 15.2 Hz, 1H), 3.79 (s, 3H), 3.55 (d, J ¼ 14.4 Hz, 1H), 1.77 (s, 3H)
13
3
.77 (d, J ¼ 14.3 Hz, 1H), 1.62 (s, 3H) ppm. C NMR (150 MHz,
DMSO‑d 173.6, 144.6, 142.8, 140.9, 138.5, 130.3, 129.4, 129.2,
6
) d
13
127.9, 127.7, 127.2, 126.3, 76.5, 64.2, 61.1, 22.9 ppm.
6
ppm. C NMR (150 MHz, DMSO‑d ) d 174.0, 158.5, 143.4, 143.0,
137.6, 134.9, 134.4, 129.1, 128.1, 128.0, 127.3, 126.3, 114.5, 76.8, 65.9,
4.2.5. N-(3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-phenylpropyl)-
55.8, 22.9 ppm.
N-(p-tolyl)acetamide (3e)
White solid (66.5 mg, 75%), m.p. 158.3e158.9 C. 1H NMR
600 MHz, DMSO‑d
7.75e7.73 (m, 2H), 7.31 (t, J ¼ 8.5 Hz, 2H),
ꢀ
4.2.11. N-(2-hydroxy-3-(naphthalen-2-ylsulfonyl)-2-
(
7
6
)
d
phenylpropyl)-N-phenylacetamide (3k)
.24 (d, J ¼ 7.0 Hz, 2H), 7.15e7.12 (m, 3H), 7.00 (d, J ¼ 7.2 Hz, 2H),
White solid (40.0 mg, 42%), m.p. 130.5e131.6 C. 1H NMR
ꢀ
6
.64e6.43 (m, 2H), 6.11 (s, 1H), 4.65 (d, J ¼ 14.4 Hz, 1H), 4.05 (d,
3
(600 MHz, CDCl ) d 7.98 (brs, 1H), 7.86e7.76 (m, 3H), 7.64e7.61 (m,
J ¼ 15.1 Hz, 1H), 3.96 (d, J ¼ 15.1 Hz, 1H), 3.70 (d, J ¼ 14.4 Hz, 1H),
2H), 7.57e7.54 (m, 1H), 7.14 (d, J ¼ 7.2 Hz, 2H), 7.09 (d, J ¼ 7.7 Hz,
2H), 6.93e6.88 (m, 3H), 6.75 (d, J ¼ 6.9 Hz, 2H), 4.84 (d, J ¼ 14.5 Hz,
1H), 4.11 (d, J ¼ 15.4 Hz, 1H), 3.84 (d, J ¼ 15.4 Hz, 1H), 3.49 (d,
1
3
2
.24 (s, 3H), 1.61 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d
65.0 (d, J ¼ 251.7 Hz), 142.9, 142.2, 138.4, 137.1, 131.5 (d, J ¼ 9.8 Hz),
31.5 (d, J ¼ 9.8 Hz), 129.9, 128.0, 127.7, 127.2, 126.3, 116.3, 116.2 (d,
J ¼ 22.7 Hz), 116.1, 76.6, 64.3, 61.3, 22.9, 21.0 ppm.
6
) d 173.7,
1
1
13
J ¼ 14.4 Hz, 1H), 2.34 (s, 3H), 1.80 (s, 3H) ppm. C NMR (150 MHz,
6
DMSO‑d ) d 173.7, 143.0,142.2,139.3,137.1,135.0,132.0,129.9,129.9,
129.5, 129.4, 128.2, 127.9, 127.8, 127.7, 127.2, 126.3, 125.1, 123.6, 76.7,
4
.2.6. N-(3-((4-chlorophenyl)sulfonyl)-2-hydroxy-2-phenylpropyl)-
N-(p-tolyl)acetamide (3f)
White solid (67.3 mg, 74%), m.p. 158.5e159.1 C. 1H NMR
600 MHz, DMSO‑d
7.70 (d, J ¼ 8.2 Hz, 2H), 7.56 (d, J ¼ 8.3 Hz,
H), 7.25 (d, J ¼ 7.3 Hz, 2H), 7.16e7.12 (m, 3H), 6.99 (d, J ¼ 7.2 Hz,
H), 6.62e6.45 (m, 2H), 6.14 (s, 1H), 4.66 (d, J ¼ 14.4 Hz,1H), 4.07 (d,
64.3, 61.2, 22.9, 21.0 ppm. HRMS (ESI) calc. for C28
(M þ Na) : 496.1553. found:496.1558.
H
27NO
4
S
þ
ꢀ
(
2
2
6
)
d
4.2.12. N-(2-(4-fluorophenyl)-2-hydroxy-3-(phenylsulfonyl)
propyl)-N-phenylacetamide (3l)
White solid (53.6 mg, 63%), m.p. 151.2e152.0 C. 1H NMR
ꢀ
J ¼ 15.1 Hz, 1H), 3.98 (d, J ¼ 15.1 Hz, 1H), 3.71 (d, J ¼ 14.4 Hz, 1H),
(600 MHz, CDCl
3
)
d
7.58 (d, J ¼ 7.3 Hz, 2H), 7.55e7.52 (m, 1H),
1
3
2
1
1
.23 (s, 3H), 1.60 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d
43.0,142.2,141.0,138.5,137.1,130.3,129.9,129.2,128.0,127.7, 127.2,
26.3, 76.6, 64.2, 61.4, 22.9, 21.0 ppm.
6
)
d
173.8,
7.39e7.37 (m, 2H), 7.30e7.29 (m, 3H), 7.16e7.10 (m, 2H), 6.87 (d,
J ¼ 4.8 Hz, 2H), 6.75 (t, J ¼ 7.7 Hz, 2H), 4.85 (d, J ¼ 14.4 Hz, 1H), 3.98
(d, J ¼ 15.3 Hz, 1H), 3.74 (d, J ¼ 15.2 Hz, 1H), 3.55 (d, J ¼ 14.4 Hz, 1H),
1
3
6
1.81 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d ) d 178.2, 166.4 (d,
4
.2.7. N-(3-((4-bromophenyl)sulfonyl)-2-hydroxy-2-
phenylpropyl)-N-(p-tolyl)acetamide (3g)
Light yellow solid (64.0 mg, 64%), m.p. 162.6e163.7 C. H NMR
600 MHz, DMSO‑d
7.70 (d, J ¼ 8.4 Hz, 2H), 7.62 (d, J ¼ 8.2 Hz,
H), 7.25 (d, J ¼ 7.3 Hz, 2H), 7.18e7.12 (m, 3H), 6.99 (d, J ¼ 7.3 Hz,
H), 6.66e6.34 (m, 2H), 6.14 (s, 1H), 4.66 (d, J ¼ 14.3 Hz,1H), 4.07 (d,
J ¼ 242.9 Hz), 149.3, 146.8, 143.7, 138.2, 134.2, 133.9, 133.2 (d,
J ¼ 8.1 Hz), 132.9, 132.7, 119.2, 81.1, 68.9, 65.5, 27.7 ppm.
ꢀ
1
(
2
2
6
)
d
4.2.13. N-(2-(4-chlorophenyl)-2-hydroxy-3-(phenylsulfonyl)
propyl)-N-phenylacetamide (3m)
White solid (61.2 mg, 69%), m.p. 174.6e175.5 C. 1H NMR
ꢀ
J ¼ 15.1 Hz, 1H), 3.97 (d, J ¼ 15.1 Hz, 1H), 3.71 (d, J ¼ 14.4 Hz, 1H),
(600 MHz, DMSO‑d
6
)
d
7.68 (d, J ¼ 7.5 Hz, 2H), 7.63 (t, J ¼ 7.2 Hz,1H),
1
3
2
.23 (s, 3H), 1.60 (s, 3H) ppm. C NMR (150 MHz, DMSO‑d
6
)
d
173.8,
7.50 (t, J ¼ 7.5 Hz, 2H), 7.27 (d, J ¼ 8.1 Hz, 2H), 7.24e7.16 (m, 3H), 7.11
142.9, 142.2, 141.4, 137.1, 132.2, 130.4, 129.9, 128.0, 127.7, 127.6, 127.2,
(d, J ¼ 8.0 Hz, 2H), 6.84e6.70 (m, 2H), 5.97 (s, 1H), 4.62 (d,
7