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Triethylamine → (RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester

HRID 602804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 602804
[CH3:1][O:2][C:3](=[O:28])[C:4]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])([CH:6]1[CH2:18][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)[CH3:5].C(N(CC)CC)C.[O:36](C(OC(C)(C)C)=O)[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:40]([O:39][C:37]([N:10]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=2[C:8]2[CH2:7][CH:6]([C:4]([S:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)(=[O:21])=[O:20])([C:3]([O:2][CH3:1])=[O:28])[CH3:5])[CH2:18][C:9]1=2)=[O:36])([CH3:43])([CH3:42])[CH3:41]
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11430019(RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester

Produkt 1

HCID 67266834(RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl esterAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

130 mg (0.31 mmol) (RS,SR)-2-benzenesulfonyl-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester were dissolved in 7 mL CH2Cl2 at RT. 90 μL (0.62 mmol, 2 eq) triethylamine, 4 mg (0.031 mmol, 0.1 eq) DMAP and 81 mg (0.37 mmol, 1.2 eq) BOC2O were added. The reaction mixture was stirred for 2 hours. The reaction was quenched with 10 mL of an aqueous 1M solution of HCl. The organic layer was separated and the aquous layer was washed with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and evaporated to dryness to yield to 152 mg (94%) (RS,SR)-2-(1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-7-chloro-2,3-dihydro-1H-cyclopenta[b]indole-4-carboxylic acid tert-butyl ester as a white powder, M: 535 (MNH4+).

Aufarbeitung

  1. customThe reaction was quenched with 10 mL of an aqueous 1M solution of HCl
  2. customThe organic layer was separated
  3. washthe aquous layer was washed with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b5e7f900249445efa9a4b9212628d74e
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07906546B2

Notizen zur Reaktion

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