The Journal of Organic Chemistry
Article
193.6, 161.3, 134.3, 134.2, 129.0, 128.0, 45.0. HRMS (ESI) m/z: [M
6H), 1.62 (td, J1 = 14.4 Hz, J2 = 4.4 Hz, 1H), 1.21−1.50 (m, 7H),
1.08 (s, 3H), 0.88 (d, J = 6.4 Hz, 3H). 13C{1H} NMR (100 MHz,
CDCl3) δ 212.0, 209.2, 208.8, 194.4, 173.6, 134.4, 134.1, 128.9, 127.9,
56.9, 51.7, 49.0, 46.8, 46.4, 45.6, 45.5, 45.0, 42.8, 38.6, 36.5, 36.0,
35.6, 35.2, 33.5, 31.1, 27.6, 25.1, 21.9, 18.8, 11.9. HRMS (ESI) m/z:
+
+ Na]+ calcd for C9H9NNaO2 186.0525; found, 186.0527.
N-(2-Oxo-2-Phenylethyl)Acetamide (3ap). Eluent: petroleum
ether/ethyl acetate (1:1). Yellowish solid (35.1 mg, 66%), mp: 85−
86 °C. 1H NMR (400 MHz, CDCl3) δ 7.97−7.99 (m, 2H), 7.62 (tt, J1
= 7.6 Hz, J2 = 1.6 Hz, 1H), 7.49 (t, J = 7.6 Hz, 2H), 6.75 (br s, 1H),
4.78 (d, J = 4.4 Hz, 2H), 2.11 (s, 3H). 13C{1H} NMR (150 MHz,
CDCl3) δ 194.3, 170.4, 134.4, 134.2, 128.9, 127.9, 46.6, 23.0. HRMS
+
[M + Na]+ calcd for C32H41NNaO5 542.2877; found, 542.2869.
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-Hydroxy-
2,4a,6a,6b,9,9,12a-Heptamethyl-13-Oxo-N-(2-Oxo-2-Phenylethyl)-
1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-Icosahydro-
picene-2-Carboxamide (3ax). Eluent: petroleum ether/ethyl acetate
+
(ESI) m/z: [M + Na]+ calcd for C10H11NNaO2 200.0682; found,
200.0680.
1
(1:1). Yellowish solid (142.6 mg, 81%), mp: 143−145 °C. H NMR
N-(2-Oxo-2-Phenylethyl)Pivalamide (3aq). Eluent: petroleum
ether/ethyl acetate (3:1). Brown oil (50.6 mg, 77%). 1H NMR
(400 MHz, CDCl3) δ 7.97−7.99 (m, 2H), 7.60−7.64 (m, 1H), 7.50
(t, J = 7.6 Hz, 2H), 6.82 (br s, 1H), 4.74 (d, J = 4.4 Hz, 2H), 1.28 (s,
9H). 13C{1H} NMR (150 MHz, CDCl3) δ 194.5, 178.7, 134.5, 134.1,
128.9, 127.9, 46.5, 38.8, 27.6. HRMS (ESI) m/z: [M + Na]+ calcd for
(400 MHz, CDCl3) δ 7.97−8.00 (m, 2H), 7.61 (t, J = 7.2 Hz, 1H),
7.49 (t, J = 8.0 Hz, 2H), 6.86 (t, J = 4.4 Hz, 1H), 5.78 (s, 1H), 4.77
(qd, J1 = 12.8 Hz, J2 = 4.0 Hz, 2H), 3.23 (dd, J1 = 11.2 Hz, J2 = 5.2
Hz, 1H), 2.77−2.81 (m, 1H), 2.35 (s. 1H), 2.26 (dd, J1 = 13.2 Hz, J2
= 3.2 Hz, 1H), 1.58−2.08 (m, 10H), 1.40−1.46 (m, 8H), 1.18−1.25
(m, 4H), 1.12 (d. J = 5.2 Hz, 6H), 0.96−1.05 (m, 5H), 0.81 (d, J =
0.4 Hz, 6H), 0.70 (d, J = 11.2 Hz, 1H). 13C{1H} NMR (100 MHz,
CDCl3) δ 200.1, 194.6, 176.2, 169.0, 134.5, 134.1, 128.9, 128.6, 128.0,
78.6, 61.8, 54.9, 47.9, 46.3, 45.4, 43.8, 43.2, 41.6, 39.2, 39.1, 37.5,
37.1, 32.8, 31.9, 31.5, 29.6, 28.4, 28.2, 27.3, 26.5, 26.4, 23.4, 18.7,
+
C13H17NNaO2 242.1151; found 242.1152.
N-(2-Oxo-2-Phenylethyl)Hexanamide (3ar). Eluent: petroleum
ether/ethyl acetate (3:1). Yellowish solid (43.4 mg, 62%), mp: 69−71
1
°C. H NMR (400 MHz, CDCl3) δ 7.97−8.00 (m, 2H), 7.60−7.64
(m, 1H), 7.50 (t, J = 7.6 Hz, 2H), 6.65 (br s, 1H), 4.78 (d, J = 4.0 Hz,
2H), 2.31 (t, J = 8.0 Hz, 2H), 1.66−1.73 (m, 2H), 1.32−1.37 (m,
4H), 0.89−0.92 (m, 3H). 13C{1H} NMR (150 MHz, CDCl3) δ
194.5, 173.4, 134.4, 134.1, 128.9, 127.9, 46.4, 36.5, 31.5, 25.4, 22.4,
+
17.5, 16.4, 15.7. HRMS (ESI) m/z: [M + H]+ calcd for C38H54NO4
588.4047; found, 588.4030.
6-(3-((3r,5r,7r)-Adamantan-1-yl)-4-Methoxyphenyl)-N-(2-Oxo-2-
Phenylethyl)-2-Naphthamide (3ay). Eluent: petroleum ether/ethyl
+
13.9. HRMS (ESI) m/z: [M + Na]+ calcd for C14H19NNaO2
1
acetate (3:1). Brown solid (87.3 mg, 55%), mp: 200−202 °C. H
256.1308; found, 256.1306.
N-(2-Oxo-2-Phenylethyl)Cyclohexanecarboxamide (3as). Eluent:
NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 8.00−8.05 (m, 3H), 7.93−
7.98 (m, 3H), 7.79 (dd, J1 = 8.8 Hz, J2 = 1.6 Hz, 1H), 7.60−7.63 (m,
2H), 7.47−7.54 (m, 4H), 6.98 (d, J = 8.4 Hz, 1H), 5.00 (d, J = 4.4
Hz, 2H), 3.88 (s, 3H), 2.19 (s, 6H), 2.11 (s, 3H), 1.80 (s, 6H).
13C{1H} NMR (100 MHz, CDCl3) δ 194.4, 167.5, 158.9, 140.9,
139.0, 135.4, 134.4, 134.3, 132.6, 131.4, 130.6, 129.4, 129.0, 128.6,
128.1, 127.6, 126.6, 126.0, 125.7, 124.7, 124.0, 112.1, 55.2, 47.1, 40.7,
37.24, 37.17, 29.2. HRMS (ESI) m/z: [M + Na]+ calcd for
petroleum ether/ethyl acetate (3:1). Yellowish solid (50.7 mg, 69%),
1
mp: 111−113 °C. H NMR (400 MHz, CDCl3) δ 7.97−7.99 (m,
2H), 7.62 (tt, J1 = 7.6 Hz, J2 = 1.2 Hz, 1H), 7.50 (t, J = 7.6 Hz, 2H),
6.63 (br s, 1H), 4.76 (d, J = 4.4 Hz, 2H), 2.25 (tt, J1 = 12.0 Hz, J2 =
3.6 Hz, 1H), 1.93 (dd, J1 = 13.2 Hz, J2 = 1.6 Hz, 2H), 1.80−1.84 (m,
2H), 1.67−1.71 (m, 1H), 1.50 (qd, J1 = 12.0 Hz,J2 = 3.2 Hz, 2H),
1.21−1.36 (m, 3H). 13C{1H} NMR (150 MHz, CDCl3) δ 194.6,
176.3, 134.5, 134.1, 128.9, 127.9, 46.3, 45.3, 29.7, 25.75, 25.72.
+
C36H35NNaO3 552.2509; found, 552.2503.
4-([1,1’-Biphenyl]-4-yl)-4-Oxo-N-(2-Oxo-2-Phenylethyl)-
Butanamide (3az). Eluent: petroleum ether/ethyl acetate (3:1). Pink
solid (75.7 mg, 68%), mp: 169−171 °C. 1H NMR (400 MHz,
CDCl3) δ 8.06 (d, J = 8.4 Hz, 2H), 7.96−7.98 (m, 2H), 7.67 (d, J =
8.4 Hz, 2H), 7.59−7.63 (m, 3H), 7.47 (q, J = 8.4 Hz, 4H), 7.37−7.41
(m, 1H), 6.88 (br s, 1H), 4.79 (d, J = 4.4 Hz, 2H), 3.43 (t, J = 6.4 Hz,
2H), 2.80 (t, J = 6.8 Hz, 2H). 13C{1H} NMR (150 MHz, CDCl3) δ
198.4, 194.2, 172.3, 145.9, 139.9, 135.3, 134.5, 134.1, 128.98, 128.95,
128.7, 128.3, 128.0, 127.30, 127.27, 46.6, 33.9, 30.1. HRMS (ESI) m/
+
HRMS (ESI) m/z: [M + Na]+ calcd for C15H19NNaO2 268.1308;
found, 268.1303.
(3R,5R,7R)-N-(2-Oxo-2-Phenylethyl)Adamantane-1-Carboxa-
mide (3at). Eluent: petroleum ether/ethyl acetate (3:1). Yellowish
solid (58.8 mg, 66%), mp: 127−128 °C. 1H NMR (400 MHz,
CDCl3) δ 7.97−8.00 (m, 2H), 7.60−7.64 (m, 1H), 7.50 (t, J = 7.2
Hz, 2H), 6.78 (br s, 1H), 4.74 (d, J = 4.4 Hz, 2H), 2.07 (s, 3H), 1.94
(d, J = 2.8 Hz, 6H), 1.71−1.79 (m, 6H). 13C{1H} NMR (150 MHz,
CDCl3) δ 194.7, 178.2, 134.5, 134.1, 128.9, 127.9, 46.3, 40.8, 39.2,
+
z: [M + Na]+ calcd for C24H21NNaO3 394.1414; found, 394.1403.
+
36.5, 28.1. HRMS (ESI) m/z: [M + Na]+ calcd for C19H23NNaO2
4-(N,N-Dipropylsulfamoyl)-N-(2-Oxo-2-Phenylethyl)Benzamide
320.1621; found 320.1612.
2-Cyano-N-(2-Oxo-2-Phenylethyl)Acetamide (3au). Eluent: pe-
(3ba). Eluent: petroleum ether/ethyl acetate (1:1). Yellowish solid
1
(88.1 mg, 73%), mp: 108−109 °C. H NMR (400 MHz, CDCl3) δ
troleum ether/ethyl acetate (5:1). Yellowish solid (47.3 mg, 78%),
7.99−8.01 (m, 4H), 7.87 (d, J = 8.4 Hz, 2H), 7.64 (t, J = 7.2 Hz, 1H),
7.51 (t, J = 8.0 Hz, 3H), 4.95 (d, J = 4.8 Hz, 2H), 3.09 (t, J = 7.6 Hz,
4H), 1.50−1.59 (m, 4H), 0.87 (t, J = 7.6 Hz, 6H). 13C{1H} NMR
(100 MHz, CDCl3) δ 194.0, 166.0, 143.0, 137.3, 134.32, 134.26,
129.0, 127.98, 127.95, 127.2, 49.9, 46.9, 21.9, 11.1. HRMS (ESI) m/z:
[M + Na]+ calcd for C21H26N2NaO4S+ 425.1505; found, 425.1496.
3-(4,5-Diphenyloxazol-2-yl)-N-(2-Oxo-2-Phenylethyl)-
Propanamide (3bb). Eluent: petroleum ether/ethyl acetate (1:1).
White solid (82.4 mg, 67%), mp: 105−106 °C. 1H NMR (400 MHz,
CDCl3) δ 7.95 (d, J = 7.2 Hz, 2H), 7.63−7.65 (m, 2H), 7.54−7.59
(m, 3H), 7.45 (d, J = 7.6 Hz, 2H), 7.28−7.36 (m, 6H), 7.08 (br s,
1H), 4.78 (d, J = 4.4 Hz, 2H), 3.24 (t, J = 7.6 Hz, 2H), 2.91 (t, J = 7.6
Hz, 2H). 13C{1H} NMR (100 MHz, CDCl3) δ 194.2, 171.5, 162.3,
145.5, 135.1, 134.4, 134.1, 132.5, 129.0, 128.9, 128.7, 128.6, 128.5,
128.1, 127.98, 127.97, 126.5, 46.6, 32.8, 24.0. HRMS (ESI) m/z: [M
1
mp: 156−157 °C. H NMR (400 MHz, CDCl3) δ 7.97−7.99 (m,
2H), 7.66 (t, J = 7.6 Hz, 1H), 7.53 (t, J = 7.6 Hz, 2H), 7.14 (br s,
1H), 4.80 (d, J = 4.4 Hz, 2H), 3.50 (s, 2H). 13C{1H} NMR (150
MHz, CDCl3) δ 193.0, 161.1, 134.6, 134.0, 129.1, 128.0, 114.2, 46.8,
+
25.9. HRMS (ESI) m/z: [M + Na]+ calcd for C11H10N2NaO2
225.0634; found 225.0634.
2-Acetamido-N-(2-Oxo-2-Phenylethyl)Acetamide (3av). Eluent:
petroleum ether/ethyl acetate (1:2). White solid (38.6 mg, 55%), mp:
1
177−178 °C. H NMR (400 MHz, CDCl3) δ 7.96−7.98 (m, 2H),
7.63 (tt, J1 = 7.6 Hz, J2 = 2.0 Hz, 1H), 7.50 (t, J = 7.6 Hz, 2H), 7.15
(br s, 1H), 6.56 (br s, 1H), 4.78 (d, J = 4.4 Hz, 2H), 4.08 (d, J = 5.2
Hz, 2H), 2.08 (s, 3H). 13C{1H} NMR (150 MHz, CDCl3) δ 193.8,
170.8, 169.2, 134.30, 134.27, 129.0, 128.0, 46.4, 43.1, 23.0. HRMS
+
(ESI) m/z: [M + Na]+ calcd for C12H14N2NaO3 257.0897; found
+
+ H]+ calcd for C26H23N2O3 411.1703; found, 411.1690.
257.0893.
2-(4-Isobutylphenyl)-N-(2-Oxo-2-Phenylethyl)Propanamide
(3bc). Eluent: petroleum ether/ethyl acetate (5:1). White solid (85.3
mg, 88%), mp: 81−82 °C. 1H NMR (600 MHz, CDCl3) δ 7.92−7.93
(m, 2H), 7.59 (t, J = 7.8 Hz, 1H), 7.47 (t, J = 7.8 Hz, 2H), 7.26 (d, J
= 8.4 Hz, 2H), 7.14 (d, J = 7.8 Hz, 2H), 6.51 (br s, 1H), 4.64−4.77
(m, 2H), 3.67 (q, J = 7.2 Hz, 1H), 2.46 (d, J = 6.6 Hz, 2H), 1.83−
1.89 (m, 1H), 1.56 (d, J = 7.2 Hz, 3H), 0.91 (d, J = 6.6 Hz, 6H).
(R)-4-((5S,8R,9S,10S,13R,14S,17R)-10,13-Dimethyl-3,7,12-Trioxo-
hexadecahydro-1H-Cyclopenta[a]Phenanthren-17-yl)-N-(2-Oxo-2-
Phenylethyl)Pentanamide (3aw). Eluent: petroleum ether/ethyl
1
acetate (1:1). White solid (101.3 mg, 65%), mp: 189−190 °C. H
NMR (400 MHz, CDCl3) δ 7.97−7.99 (m, 2H), 7.62 (t, J = 7.2 Hz,
1H), 7.50 (t, J = 7.6 Hz, 2H), 6.67 (t, J = 4.0 Hz, 1H), 4.77 (d, J = 4.4
Hz, 2H), 2.82−2.95 (m, 3H), 2.11−2.46 (m, 10H), 1.81−2.04 (m,
H
J. Org. Chem. XXXX, XXX, XXX−XXX