4-Methylmorpholine → (R,S)-Benthiavalicarb-isopropyl

HRID 1531408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531408
[CH:1]([O:4][C:5]([NH:7][C@@H:8]([C:12]([OH:14])=O)[CH:9]([CH3:11])[CH3:10])=[O:6])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:41][C:42]1[CH:53]=[CH:52][C:45]2[N:46]=[C:47]([C@@H:49]([NH2:51])[CH3:50])[S:48][C:44]=2[CH:43]=1>C1(C)C=CC=CC=1>[F:41][C:42]1[CH:53]=[CH:52][C:45]2[N:46]=[C:47]([C@@H:49]([NH:51][C:12]([C@H:8]([NH:7][C:5](=[O:6])[O:4][CH:1]([CH3:2])[CH3:3])[CH:9]([CH3:10])[CH3:11])=[O:14])[CH3:50])[S:48][C:44]=2[CH:43]=1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 53692456(2R)-3-methyl-2-{[(propan-2-yloxy)carbonyl]amino}butanoic acidHCID 86756512(S)-1-(6-fluoro-2-benzothiazolyl)ethylamine p-toluenesulfonate

Produkt 1

HCID 86756513(R,S)-Benthiavalicarb-isopropylAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In 250 ml of toluene, 13.4 g (0.066 mol) of N-isopropoxycarbonyl-D-valine was dissolved. Thereto was added 14.3 g (0.144 mol) of N-methylmorpholine. Then was dropwise added at −10° C., 8.6 g (0.063 mol) of isobutyl chlorocarbonate. Thereto was added 22 g (0.06 mol) of (S)-1-(6-fluoro-2-benzothiazolyl)ethylamine p-toluenesulfonate. A reaction and a post-treatment were conducted in the same manner as in Reference Example 1, and the hot toluene solution was filtered in a hot state to remove the insoluble matter. The filtrate was cooled, whereby crystals were precipitated. The crystals were collected by filtration and dried to obtain 15.8 g (yield: 69.3%) of isopropyl {(R)-1-[(S)-1-(6-fluorobenzothiazol-2-yl)ethylcarbamoyl]-2-methylpropyl}carbamate. The compound obtained was confirmed for the structure by IR analysis and NMR analysis in comparison with its authentic material and identified.

Aufarbeitung

  1. additionThen was dropwise added at −10° C.
  2. customA reaction
  3. filtrationthe hot toluene solution was filtered in a hot state
  4. customto remove the insoluble matter
  5. temperatureThe filtrate was cooled
  6. customwhereby crystals were precipitated
  7. filtrationThe crystals were collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3fcd28bad8a14953980d98313f78e473
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06197969B1

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