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Water → tert. Butyl (3SR,4SR)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylate

HRID 1875329
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Reaktionsgleichung

Reaktionsgleichung von HRID 1875329
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:32][CH:33]1[CH:37]([OH:38])[CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1.O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:32][CH:33]2[CH:37]([OH:38])[CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]2)=[O:9])=[CH:4][CH:3]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11229445tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 74835283tert. Butyl (3SR,4SR)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

201 mg (1.2 mmol) 5-chlorothiophene-2-carboxylic acid and 436 mg (1.4 mmol) TBTU are suspended in 5 ml DCM and combined with 260 μl (1.9 mmol) TEA. The mixture is stirred for 30 minutes and then a solution of 250 mg (1.2 mmol) tert. Butyl (3SR,4SR)-3-amino-4-hydroxy-pyrrolidine-1-carboxylate in 5 ml DCM is added and the mixture is stirred for 16 hours at RT. Then the reaction mixture is poured into water and extracted with DCM. The organic phase is washed with sat. sodium chloride solution and, after being mixed with activated charcoal, dried on sodium sulphate. The mixture is filtered and the filtrate is evaporated to dryness. The residue thus obtained is purified by column chromatography (silica gel, eluant DCM/MeOH 10:1).

Aufarbeitung

  1. stirringthe mixture is stirred for 16 hours at RT
  2. extractionextracted with DCM
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. additionafter being mixed with activated charcoal
  5. customdried on sodium sulphate
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated to dryness
  8. customThe residue thus obtained
  9. customis purified by column chromatography (silica gel, eluant DCM/MeOH 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac3d6ee1ae6d4d22b9676ccfd73faca3
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309542B2

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