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p-Bromobenzenesulfonyl chloride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

HRID 926010
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 926010
[OH:1][C@@H:2]1[CH2:27][CH2:26][C@H:5]2[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]3[CH2:19][C@@:15]3([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]2[CH2:3]1.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([O:1][C@@H:2]2[CH2:27][CH2:26][C@H:5]3[C:6](=[O:25])[N:7]([CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C@@H:14]4[CH2:19][C@@:15]4([C:20]([O:22][CH3:23])=[O:21])[NH:16][C:17](=[O:18])[C@@H:4]3[CH2:3]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1
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Komponenten

5

Edukt 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 69915043(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Produkt 1

HCID 88050650(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(4-bromophenylsulfonyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of compound 43 (0.13 mmol), TEA (0.39 mmol), and DMAP (0.009 mmol) in anhydrous DCM (0.3 mL) was added 4-bromobenzenesulfonyl chloride (0.17 mmol) in DCM (0.15 mL) dropwise. The reaction mixture was stirred at room temperature under nitrogen for 16 hrs. The crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3. The organics were concentrated to yield compound 44 as a yellow oil in a quantitative yield. MS (ESI, EI+): m/z=598 (MH+).

Aufarbeitung

  1. washThe crude material was washed sequentially with 0.5N HCl and 2.5% NaHCO3
  2. concentrationThe organics were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-72edad27e9154592ae93de74eedfed18
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09284307B2

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