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Potassium Hydroxide → (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamic-acid

HRID 975943
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HRID 975943 반응식
[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)/[CH:27]=[CH:28]/[C:29]([O:31]CC)=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO.O>[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 86750515ethyl (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamate

생성물 1

HCID 19967985(E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamic-acid수율 28.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962
Water
용매

실험 절차

By proceeding in a fashion similar to that described in Example 9, but starting from 3.7 g of ethyl (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamate in solution in 60 cm3 of methanol and 0.4 g of potassium hydroxide dissolved in 20 cm3 of water and after treatment, 1 g of (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamic-acid is obtained [proton NMR (250 MHz, DMSO D6, δ in ppm, J in Hz), 2 rotamers at room temperature, preponderant rotamer description, general description valid for the other products of the series: 1.5 (bs, 9H, (CH3)3 ; 1.9 and 2.2 (2m, 4H, H in position 3 and 4 on pyrrolidine); 3.2 and 3.9 (ABX, 2H, CH2N); 4.35 (dd, 1H, H in position 2 on pyrrolidine); 5.20 (dd, 1H, H in position 5 on pyrrolidine); 6.30 (dd, 1H, NH); 6.4 (bd, 1H, J=15, CH= trans); 7.1 to 7.7 (m, 10H, aromatic and CH= trans); (s, 1H, NH). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 3075, 3030, 3700 to 2250 with a maximum at 2475, 2980, 2935, 2875, 1735, 1705, 1695, 1640, 1610, 1590, 1560, 1495, 1450, 1430, 1395, 1370, 1315, 1250, 1225, 1155, 985, 910, 890, 860, 840, 790, 760, 705, 685].

출처 및 근거

ORD 기록
ord-4d8bdcb7f1784add902ca47d16ce0138
출처 데이터셋
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05610144

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