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Trifluoroacetic acid → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3S*,4S*)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

HRID 1158490
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HRID 1158490 반응식
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH3:25])[S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C@H:10]([CH2:26][N:27]([CH:44]([CH3:46])[CH3:45])[C:28](=[O:43])[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:44]([N:27]([CH2:26][C@H:10]1[C@H:11]([CH2:13][N:14]([CH3:25])[S:15]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:16])=[O:17])[CH2:12][NH:8][CH2:9]1)[C:28](=[O:43])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)([CH3:46])[CH3:45]
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68643106(3R*,4S*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 59512513N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-{(3S*,4S*)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidin-3-ylmethyl}-benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3R*,4S*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-[(methyl-phenylmethanesulfonyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (49 mg, 0.074 mmol) in 2 mL CH2Cl2, TFA (86 μL, 1.11 mmol) is added. The mixture is stirred 4 h at RT and then poured into a saturated solution of NaHCO3. The layers are separated, and the aqueous one is back-extracted twice with CH2Cl2. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 95:5) to give the title product. TLC, Rf (CH2Cl2/MeOH 9:1)=0.2. MS (LC-MS): 563.0 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.55 min.

후처리

  1. customThe layers are separated
  2. extractionthe aqueous one is back-extracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 95:5)

출처 및 근거

ORD 기록
ord-affd8f161e804ea7b8287be907c4ee61
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07807709B2

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