Dimethyl Sulfoxide → {1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

HRID 1180770ノート

反応式

HRID 1180770 の反応式
[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:39])[O:21][CH2:22][C:23]1([CH2:27][C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:32]=2)[CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CCCCCC>[O:13]=[C:3]([NH:4][C@@H:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:6])[C:2]([C@@H:14]([NH:19][C:20](=[O:39])[O:21][CH2:22][C:23]1([CH2:27][C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:32]=2)[CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11753176{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate

生成物 1

HCID 11295769{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate収率 96%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

To a solution of 0.2 g (0.364 mmol) of {1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate in 3 mL of dichloromethane cooled to −60° C. was added 0.079 mL (0.91 mmol) of oxalyl chloride and—0.129 mL (1.82 mmol) od dimethylsulfoxide, followed by the addition of 0.204 mL (1.45 mmol) of triethylamine. After stirring for 15 min, the reaction was warmed to room temperature and applied directly to a silica gel column using ethyl acetate:hexane (3:7) as the eluent to afford 0.19 g (96%) of {1-[(4-phenyl-1,3-thiazol-2-yl)methyl]cyclobutyl}methyl (1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 9.21 (d, J=8 Hz, 1H), 7.98 (m, 3H), 7.64 (d, J=8 Hz, 1H), 7.25-7.23 (m, 8 H), 4.96-5.01 (m, 1H), 4.80 (m, 1H), 4.01 (s, 2H), 3.30 (s, 2H), 2.12-1.64 (m, 10 H), 1.42 (d, J=7 Hz, 3H), 1.29-1.21 (m, 2H), 0.82 (t, J=7 Hz, 3H). LC-MS m/z 548 (M+H).

出典と根拠

ORDレコード
ord-96918f06e4e54dd782e783b0ffd712ee
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

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