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Ethyl Acetate → tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate

HRID 1760811
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760811
[CH2:1]1[O:34][C:33]2[CH:32]=[CH:31][C:5]([CH2:6][N:7]([S:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[CH3:30])(=[O:20])=[O:19])[C@H:8]([CH2:16][NH2:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=2[O:2]1.C[Si](C#N)(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C(OCC)(=O)C>C(#N)C>[CH2:1]1[O:34][C:33]2[CH:32]=[CH:31][C:5]([CH2:6][N:7]([S:18]([C:21]3[C:22]([CH3:30])=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[CH3:27])(=[O:20])=[O:19])[C@H:8]([CH2:16][NH:17][S:42]([CH3:41])(=[O:44])=[O:43])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:4][C:3]=2[O:2]1
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Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 82115Trimethylsilyl cyanideHCID 69762296tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate

Produkt 1

HCID 18337582tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate
Ausbeute 122,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-amino-propionate (1.02 g, 2.0 mmol), with trimethylsilyl cyanide (0.7 ml, 5.2 mmol) in dry acetonitrile (15 ml) was added methanesulfonyl chloride (0.18 ml, 2.3 mmol) and the material was stirred overnight. Ethyl acetate (80 ml) was added and the material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml). The organic phase was collected and washed with an equal volume of brine. The aqueous phases were back extracted with ethyl acetate (2×80 ml) and the organic phases combined, dried (MgSO4), filtered and condensed to provide tert-butyl 2(R)-[(3,4-methylendioxybenzyl)-(2,6-dimethyl-4-methoxybenzenesulfonyl)amino]-3-methanesulfonylamino-propionate as a pale yellow semi-viscous oil (1.4 g).

Aufarbeitung

  1. customthe material was partitioned with aqueous hydrochloric acid (1.5%, 80 ml)
  2. customThe organic phase was collected
  3. washwashed with an equal volume of brine
  4. extractionThe aqueous phases were back extracted with ethyl acetate (2×80 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-ffec916139214d25a63f30bb204d97bc
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06844366B2

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