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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 2282827 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 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

생성물 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)-
수율 96.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-cf3bb14e709249e3b3c7660b3e762b26
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09138486B2

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