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Propylphosphonic anhydride → (2R)-2-amino-2-methyl-N-[6-[(2,4,4-trimethyl-3,1-benzoxazin-5-yl)oxy]-3-pyridyl]butanamide

HRID 527663
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 527663
[CH3:1][C:2]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]2[C:10]([O:14][C:15]3[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)=[CH:11][CH:12]=[CH:13][C:4]=2[N:3]=1.Cl.[NH2:23][C@:24]([CH3:30])([CH2:28][CH3:29])[C:25](O)=[O:26].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C.CC#N.C(OCC)(=O)C.O>[NH2:23][C@:24]([CH3:30])([CH2:28][CH3:29])[C:25]([NH:21][C:18]1[CH:19]=[N:20][C:15]([O:14][C:10]2[C:5]3[C:6]([CH3:8])([CH3:9])[O:7][C:2]([CH3:1])=[N:3][C:4]=3[CH:13]=[CH:12][CH:11]=2)=[CH:16][CH:17]=1)=[O:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 111923Propylphosphonic anhydrideHCID 17998883(R)-2-Amino-2-methylbutanoic acid hydrochlorideHCID 679602016-[(2,4,4-Trimethyl-3,1-benzoxazin-5-yl)oxy]pyridin-3-amine2×

Produkt 1

HCID 67959970(2R)-2-amino-2-methyl-N-[6-[(2,4,4-trimethyl-3,1-benzoxazin-5-yl)oxy]-3-pyridyl]butanamideAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×
HCID 21930812Acetonitrile ethyl acetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 6-[(2,4,4-trimethyl-3,1-benzoxazin-5-yl)oxy]pyridin-3-amine (Intermediate 204, 185 mg, 0.65 mmol) and (R)-2-amino-2-methyl-butanoic acid hydrochloride (100 mg, 0.67 mmol) in ethyl acetate/MeCN (2 mL, 1:3 v/v mixture), a 50% w/w solution in ethyl acetate of T3P (0.43 mL) was added drop wise at 0° C. The mixture was then heated at 60° C. for 3 hours and at 80° C. for 4.5 hours. The mixture was cooled to room temperature diluted with water (5 mL) and ethyl acetate (10 mL), Two phases were separated and the aqueous one was treated with a saturated solution of NaHCO3 (pH=8) and back-extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated and the residue was purified by flash chromatography on silica gel using cyclohexane/ethyl acetate 20:80 as eluent affording the title compound (143 mg) as a yellow foam.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customwere separated
  3. additionthe aqueous one was treated with a saturated solution of NaHCO3 (pH=8)
  4. extractionback-extracted with ethyl acetate (2×10 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e35ce4eb4320490882673310fd91ddb7
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346790B2

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