Methanol → (S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

HRID 2371322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371322
C[O:2][C:3](=[O:31])[C@@H:4]([NH:8][C:9](=[O:30])[C@@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]=[CH2:21])=[CH:14][CH:13]=1)[CH:5]([CH3:7])[CH3:6].[OH-].[Na+].CO>C1COCC1.O>[CH2:19]([O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C:9]([NH:8][C@@H:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:31])=[O:2])=[O:30])=[CH:13][CH:14]=1)[CH:20]=[CH2:21]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14632374(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid methyl ester

Produkt 1

HCID 66847200(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Methyl ester 42 (4.90 g, 11.3 mmol) was dissolved in THF (35 mL) and sodium hydroxide (17 mmol) pre-dissolved in water (10 mL) was added. A further 15 mL of THF and 20 mL of methanol were added to obtain a homogenous solution. The reaction mixture was stirred at rt for 18 h before being concentrated in vacuo. The residue was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted twice more with EtOAc and the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to yield a white foam, 4.60 g, 97%.

Aufarbeitung

  1. additionwas added
  2. customto obtain a homogenous solution
  3. concentrationbefore being concentrated in vacuo
  4. customThe residue was partitioned between EtOAc and 1M hydrochloric acid
  5. extractionThe aqueous phase was extracted twice more with EtOAc
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a white foam, 4.60 g, 97%

Quellen und Nachweise

ORD-Eintrag
ord-fc416837675b42e1b3eb90f93f559abf
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710178B2

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