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1-Hydroxybenzotriazole → 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester

HRID 408625
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 408625
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:24][O:25][C:26](=[O:46])[CH2:27][CH2:28][CH2:29][N:30]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1)[C:31]([C@@:33]1([CH3:37])[CH2:36][CH2:35][NH:34]1)=[O:32].C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1>[CH3:24][O:25][C:26](=[O:46])[CH2:27][CH2:28][CH2:29][N:30]([C:31]([C@@:33]1([CH3:37])[CH2:36][CH2:35][N:34]1[C:6]([C:4]1[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=2[S:1][CH:5]=1)=[O:8])=[O:32])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 601280Benzo(b)thiophene-3-carboxylic acidHCID 705568104-[(3-chloro-benzyl)-((R)-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride

Produkt 1

HCID 705573284-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester
Ausbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a suspension of benzo[b]thiophene-3-carboxylic acid (7.12 g, 1.2 eq.) in 210 mL of DCM and 210 mL of THF were added HOBt (5.4 g, 1.2 eq.) EDC.HCl (9.6 g, 1.5 eq.) and TEA (18.5 mL, 4 eq.). The reaction was stirred at 20° C. for 15 h, then a solution of 4-[(3-chloro-benzyl)-((R)-2-methyl-azetidine-2-carbonyl)-amino]-butyric acid methyl ester hydrochloride obtained in step i above (12.5 g, 1 eq.) in 105 mL of DCM and 105 mL of THF was added. The reaction was stirred at 20° C. for 4.5 h. The crude was diluted with DCM. A saturated aqueous solution of NaHCO3 was added. The aqueous layer was extracted three times with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 90/10 to 50/50) to afford 4-[[(R)-1-(benzo[b]thiophene-3-carbonyl)-2-methyl-azetidine-2-carbonyl]-(3-chloro-benzyl)-amino]-butyric acid methyl ester (14.53 g, yield=87%).

Aufarbeitung

  1. stirringThe reaction was stirred at 20° C. for 4.5 h
  2. extractionThe aqueous layer was extracted three times with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 90/10 to 50/50)

Quellen und Nachweise

ORD-Eintrag
ord-c0471365e74041c686816c41d600d815
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08759334B2

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