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Lithium Hydroxide → 2-[4-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoylamino]-indane-2-carboxylic acid

HRID 2405247
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2405247
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[S:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.C[O:48][C:49]([C:51]1([NH2:60])[CH2:59][C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:52]1)=[O:50].[Cl-].[Li+].[OH-].[Li+]>CN(C=O)C.C1COCC1.O.CC(=O)OCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:60][C:51]2([C:49]([OH:50])=[O:48])[CH2:52][C:53]3[C:58](=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:59]2)=[O:9])=[CH:5][C:4]=1[S:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1
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Komponenten

10

Edukt 5

HCID 3939Lithium HydroxideHCID 433294Lithium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 670766864-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoic acid

Produkt 1

HCID 444785022-[4-Methoxy-3-(2-m-tolyl-ethylsulfanyl)-benzoylamino]-indane-2-carboxylic acidAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

700 mg of the crude compound of step 2 were dissolved in 5 ml of DMF and 598 mg (4.63 mmol) of EDIA and 968 mg (2.55 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were added. Then a solution of 527 mg (2.32 mmol) of 2-amino-indane-2-carboxylic acid methyl ester hydrochloride in 5 ml of DMF was added. After stirring overnight, EA and an aqueous solution of lithium chloride (4%) were added, the organic phase was separated, washed once with a solution of lithium chloride and twice with a solution of sodium hydrogencarbonate, dried and evaporated. The solid residue was dissolved in 10 ml of a 9:1 mixture of THF and water, and 131 mg (5.47 mmol) of lithium hydroxide were added. After stirring overnight, the mixture was evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to give 222 mg of the title compound.

Aufarbeitung

  1. customthe organic phase was separated
  2. washwashed once with a solution of lithium chloride and twice with a solution of sodium hydrogencarbonate
  3. customdried
  4. customevaporated
  5. additionwere added
  6. stirringAfter stirring overnight
  7. customthe mixture was evaporated to dryness
  8. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5ffb27491cf04f55bb146007c0482bdd
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08802720B2

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