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Diethylamine → 2-Pyrrolidinepropanamide, 1-[(3R,4S,5S)-4-[[(2S)-2-[[(1-aminocyclopentyl)carbonyl]amino]-3-methyl-1-oxobutyl]methylamino]-3-methoxy-5-methyl-1-oxoheptyl]-I(2)-methoxy-I+/--methyl-N-[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]-, (I+/-R,I(2)R,2S)-

HRID 2282827
ノート
印刷プレビュー

反応式

HRID 2282827 の反応式
C1C2C(COC([NH:18][C:19]3([C:24]([NH:26][C@H:27]([C:31]([N:33]([C@@H:35]([C@@H:68]([CH3:71])[CH2:69][CH3:70])[C@H:36]([O:66][CH3:67])[CH2:37][C:38]([N:40]4[CH2:44][CH2:43][CH2:42][C@H:41]4[C@H:45]([O:64][CH3:65])[C@@H:46]([CH3:63])[C:47](=[O:62])[NH:48][C@H:49]([C:57]4[S:58][CH:59]=[CH:60][N:61]=4)[CH2:50][C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:39])[CH3:34])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]3)=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>O1CCCC1>[NH2:18][C:19]1([C:24]([NH:26][C@H:27]([C:31]([N:33]([C@@H:35]([C@@H:68]([CH3:71])[CH2:69][CH3:70])[C@H:36]([O:66][CH3:67])[CH2:37][C:38]([N:40]2[CH2:44][CH2:43][CH2:42][C@H:41]2[C@H:45]([O:64][CH3:65])[C@@H:46]([CH3:63])[C:47](=[O:62])[NH:48][C@H:49]([C:57]2[S:58][CH:59]=[CH:60][N:61]=2)[CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)=[O:39])[CH3:34])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 8021DiethylamineHCID 86685730N2-[(1-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentyl)-carbonyl]-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

生成物 1

HCID 715708742-Pyrrolidinepropanamide, 1-[(3R,4S,5S)-4-[[(2S)-2-[[(1-aminocyclopentyl)carbonyl]amino]-3-methyl-1-oxobutyl]methylamino]-3-methoxy-5-methyl-1-oxoheptyl]-I(2)-methoxy-I+/--methyl-N-[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]-, (I+/-R,I(2)R,2S)-
収率 96.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of #46 (500 mg, 0.504 mmol, 1 eq.) in tetrahydrofuran (8 mL, 0.06 M) was added diethylamine (4 mL). After stirring for 18 hours, the reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (Gradient: 0% to 10% methanol in dichloromethane) to give #47 (374 mg, 96%) as a white solid. LC-MS: m/z 769.6 [M+H+], retention time=0.70 minutes; 1H NMR (400 MHz, DMSO-d6), presumed to be a mixture of rotamers, characteristic signals: δ [8.64 (br d, J=8.4 Hz) and 8.87 (br d, J=8.6 Hz), total 1H], [8.22 (br d, J=9.4 Hz) and 8.26 (br d, J=9.4 Hz), total 1H], [7.77 (d, J=3.3 Hz) and 7.80 (d, J=3.3 Hz), total 1H], [7.63 (d, J=3.1 Hz) and 7.66 (d, J=3.3 Hz), total 1H], 7.13-7.31 (m, 5H), [5.39 (ddd, J=11.1, 8.5, 4.2 Hz) and 5.54 (ddd, J=11.7, 8.8, 4.1 Hz), total 1H], [4.53 (dd, J=9.2, 7.6 Hz) and 4.64 (dd, J=9.2, 6.6 Hz), total 1H], 3.16, 3.20, 3.21 and 3.25 (4 s, total 6H), 2.93 and 3.03 (2 br s, total 3H), [1.05 (d, J=6.8 Hz) and 1.10 (d, J=6.6 Hz), total 3H], 0.73-0.80 (m, 3H).

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography (Gradient: 0% to 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-cf3bb14e709249e3b3c7660b3e762b26
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09138486B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート