Methanesulfonyl chloride → 3-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

HRID 1504844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504844
[OH:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH:3]([NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])[CH2:4][NH:5][C:6]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:15])(=[O:27])=[O:26]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 755959732-(Boc-amino)-3-(Cbz-amino)-1-propanol

Produkt 1

HCID 867317143-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of benzyl tert-butyl (3-hydroxypropane-1,2-diyl)biscarbamate (60.0 g, 185 mmol) in DCM (1000 mL) was added methanesulfonylchloride (23 g, 200 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 12 hours, the reaction mixture was concentrated under reduced pressure and purified directly by chromatography on silica gel to give 3-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate. MS ESI calc'd. for C17H27N2O7S [M+H]+ 403. found 403. 1H NMR (400 MHz, CD3OD) δ 7.34-7.32 (m, 5), 5.17-5.07 (m, 2H), 4.18-4.16 (m, 2H), 4.09-3.91 (m, 1H), 3.29-3.28 (m, 2H), 3.05 (s, 3H), 1.42 (s, 9H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified directly by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ce87acb0f6984965ac41d9863995ff7e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216173B2

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