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

HRID 1180770노트

반응식

HRID 1180770 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-96918f06e4e54dd782e783b0ffd712ee
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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