2-Bromobenzoyl chloride → HCID 14750331, Verbindung

HRID 1165968

Reaktionsgleichung

Reaktionsgleichung von HRID 1165968
[OH:1][C@@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.C(N(C(C)C)CC)(C)C.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C1COCC1>[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:5]1[CH2:6][C@@H:2]([OH:1])[CH2:3][C@H:4]1[C:7]([O:9][CH3:10])=[O:8])=[O:24]

Komponenten

5

Edukt 3

HCID 235422-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 7021050methyl (2S,4S)-4-hydroxypyrrolidine-2-carboxylate

Produkt 1

HCID 14750331HCID 14750331, VerbindungAusbeute 55,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Into a flame-dried 100 ml three-necked round-bottomed flask containing 30 ml of distilled THF was placed 3.00 g (16.575 mmol) of (cis)-4-hydroxy-L-proline, methyl ester; the vessel was immersed in an ice/water bath and the suspension was allowed to stir under argon for 5 minutes. At this time, 6.35 ml (36.465 mmol) of diisopropylethylamine was added slowly via syringe; the mixture was allowed to stir for 10 minutes, whereupon 3.64 g (16.576 mmol) of 2-bromobenzoyl chloride was added dropwise via syringe over the course of 10 minutes. The mixture was allowed to stir at 0° for 2 hours then gradually brought to room temperature overnight. The mixture was concentrated under vacuum to a minimal volume, transferred to a separatory funnel, and diluted with 100 ml of ethyl acetate, then washed with 1N HCl (2×30 ml), saturated sodium bicarbonate (2×30 ml), and brine (30 ml). The organic solution was dried over sodium sulfate, filtered, and concentrated under vacuum. Recrystallization from hot ethyl acetate yielded 3.034 g (55.6%) of the title compound, m.p. 145.5°-146.8° C.; a second recrystallization of the mother liquor yielded 1.726 g to bring the net yield to 4.760 g (87.3%).

Aufarbeitung

  1. customthe vessel was immersed in an ice/water bath
  2. additionwas added dropwise via syringe over the course of 10 minutes
  3. stirringto stir at 0° for 2 hours
  4. waitthen gradually brought to room temperature overnight
  5. concentrationThe mixture was concentrated under vacuum to a minimal volume
  6. customtransferred to a separatory funnel
  7. additiondiluted with 100 ml of ethyl acetate
  8. washwashed with 1N HCl (2×30 ml), saturated sodium bicarbonate (2×30 ml), and brine (30 ml)
  9. dry with materialThe organic solution was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customRecrystallization from hot ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9c2a3c83e3444c3ab2ba00631a1e403a
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912231

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