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Methanol → 3-(((S)-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl)-2-oxopyrrolidin-3-yl)carbamoyl)-5-tert-butylbenzoic acid

HRID 1455394
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HRID 1455394 반응식
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C@H:7]2[CH2:12][CH2:11][C@@H:10]([N:13]([CH:15]([CH3:17])[CH3:16])[CH3:14])[CH2:9][C@H:8]2[CH2:18][CH2:19][CH3:20])[C:3]1=[O:21].[C:22]([C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([C:35](OC)=[O:36])[CH:34]=1)[C:29]([OH:31])=[O:30])([CH3:25])([CH3:24])[CH3:23].[Li+].[OH-].CO>CN(C=O)C.C(O)(C(F)(F)F)=O.O>[CH:15]([N:13]([CH3:14])[C@@H:10]1[CH2:11][CH2:12][C@H:7]([N:4]2[CH2:5][CH2:6][C@H:2]([NH:1][C:35]([C:33]3[CH:32]=[C:28]([CH:27]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:34]=3)[C:29]([OH:31])=[O:30])=[O:36])[C:3]2=[O:21])[C@H:8]([CH2:18][CH2:19][CH3:20])[CH2:9]1)([CH3:16])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 121446585-tert-Butyl-isophthalic acid monomethyl esterHCID 68767742(S)-3-amino-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl)pyrrolidin-2-one

생성물 1

HCID 687659413-(((S)-1-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl)-2-oxopyrrolidin-3-yl)carbamoyl)-5-tert-butylbenzoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 22392675Trifluoroacetic acid water용매

실험 절차

Following the method described in Example 2c, Step 4, (S)-3-amino-1-[(1S,2R,4R)-4-(isopropyl(methyl)amino)-2-propylcyclohexyl]pyrrolidin-2-one (223 mg) was coupled with 3-tert-butyl-5-(methoxycarbonyl)benzoic acid (165 mg, see Preparation H6, Step 1) in 8 mL of DMF. After 14 h, 2 mL of this reaction mixture was removed and purified to provide Example 2ba. The remaining portion of the reaction mixture was charged successively with aq. LiOH (48 mg in 2 mL water) and MeOH (1 mL) before being stirred at RT for 14 h. The mixture was diluted with 2.0% TFA/water, filtered, and purified directly by RP-HPLC to afford the titled compound. MS found: (M+H)+=500.4.

후처리

  1. custom2 mL of this reaction mixture was removed
  2. custompurified
  3. customto provide Example 2ba
  4. filtrationfiltered
  5. custompurified directly by RP-HPLC

출처 및 근거

ORD 기록
ord-950682cb5ffb4c458931651744fceb1d
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07482335B2

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