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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium Hydroxide → (+/-)-(4-Chloro-2-{2-[2-(2,4-dimethyl-thiazol-5-yl)-cyclopropanecarbonyl]-1,2,3,4-tetrahydro-isoquinolin-1-yl}-phenoxy)-acetic acid

HRID 2036207
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HRID 2036207 반응식
[CH3:1][C:2]1[S:3][C:4]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=O)=[C:5]([CH3:7])[N:6]=1.C([O:16][C:17](=[O:37])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][NH:28]1)C.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(O)=O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:17]([OH:37])=[O:16])=[C:21]([CH:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][CH2:29][N:28]2[C:11]([CH:9]2[CH2:10][CH:8]2[C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])=[O:13])[CH:22]=1
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참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66653751(+/-)-[4-Chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl esterHCID 66656330(+/-)-trans-2-(2,4-Dimethyl-thiazol-5-yl)cyclopropanecarboxylic acid

생성물 1

HCID 66653993
(+/-)-(4-Chloro-2-{2-[2-(2,4-dimethyl-thiazol-5-yl)-cyclopropanecarbonyl]-1,2,3,4-tetrahydro-isoquinolin-1-yl}-phenoxy)-acetic acid

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 284Formic Acid용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (±)-trans-2-(2,4-dimethyl-thiazol-5-yl)cyclopropanecarboxylic acid (42 mg, 0.20 mmol, 1.0 eq.) and (±)-[4-chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxy]-acetic acid ethyl ester (73 mg, 0.20 mmol, 1.0 eq.) in DMF (2.4 mL), DMAP (37 mg, 0.30 mmol, 1.5 eq.) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (58 mg, 0.30 mmol, 1.5 eq.) were added. The resulting solution was stirred at r.t. for 62 hours. 1M aq. NaOH soln. (1.2 mL) was added and the solution was stirred at r.t. for 3.5 hours. Formic acid (0.2 mL) was added. The crude mixture was purified by prep. HPLC (column: Waters XBridge, 19×50 mm, 5 um, UV/MS, acidic conditions). The two racemic diastereoisomers were separated (LC-MS 3: tR (±)-dial=0.81 and tR (±)-dia2=0.82). The title compound showed: tR=0.82.

후처리

  1. addition(1.2 mL) was added
  2. stirringthe solution was stirred at r.t. for 3.5 hours
  3. customThe crude mixture was purified by prep
  4. customThe two racemic diastereoisomers were separated (LC-MS 3

출처 및 근거

ORD 기록
ord-8a88928ca4d44ca29220cf25f94680c5
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08575158B2

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