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Hydrochloric Acid → 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

HRID 1887002
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887002
C[O:2][C:3]([C:5]1[S:6][C:7]([C:28]#[C:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:8][C:9]=1[N:10]([CH2:20][CH2:21][P:22]([O:25][CH2:26][CH3:27])([CH3:24])=[O:23])[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].[Li+].[OH-].O.Cl>C1COCC1.CO>[CH3:32][C:30]([CH3:31])([CH3:33])[C:29]#[C:28][C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([CH2:20][CH2:21][P:22]([O:25][CH2:26][CH3:27])([CH3:24])=[O:23])[C:11]([CH:13]2[CH2:14][CH2:15][CH:16]([CH3:19])[CH2:17][CH2:18]2)=[O:12])[CH:8]=1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 670337505-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 670359145-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid
Ausbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (251 mg, 0.51 mmol) was dissolved in THF (7.3 mL) and MeOH (7.3 mL). A 1N solution of LiOH in H2O (1.52 mL, 1.52 mmol) was added to the reaction drop-wise at room temperature. The reaction was run at room temperature until complete, as determined by LC/MS. The reaction was cooled in an ice bath and then acidified to pH 3 with 1N HCl. The entire mixture was then evaporated in vacuo and stored under high vacuum overnight. 5-(3,3-Dimethyl-but-1-ynyl)-3-[[2-(ethoxy-methyl-phosphinoyl)-ethyl]-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (168 mg, 69%) was isolated from the residue by reverse phase HPLC. MS (m/z): 481.93 [M+H]+; 31P NMR (161.9 MHz, CDCl3): d 56.771, 55.816.

Aufarbeitung

  1. customwas run at room temperature
  2. temperatureThe reaction was cooled in an ice bath
  3. customThe entire mixture was then evaporated in vacuo
  4. customstored under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-1e7f898e04d64535961d4dcf9b461fe7
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501714B2

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