Bromotrimethylsilane → (1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester

HRID 1516423

Reaktionsgleichung

Reaktionsgleichung von HRID 1516423
[CH3:1][O:2][C:3](=[O:52])[NH:4][C@H:5]([C:19](=[O:51])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]([N:36]([S:41]([C:44]1[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=1)(=[O:43])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:26][O:27][P:28]([O:33]CC)([O:30]CC)=[O:29])[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Si](Br)(C)C>ClCCl>[CH3:1][O:2][C:3](=[O:52])[NH:4][C@H:5]([C:19](=[O:51])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C@H:25]([N:36]([S:41]([C:44]1[CH:45]=[CH:46][C:47]([NH2:50])=[CH:48][CH:49]=1)(=[O:42])=[O:43])[CH2:37][CH:38]([CH3:40])[CH3:39])[CH2:26][O:27][P:28]([OH:33])([OH:30])=[O:29])[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 76113BromotrimethylsilaneHCID 24778259(1S,5S)-{1-[5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-(diethoxy-phosphoryloxy)-hexylcarbamoyl]-2,2-diphenyl-ethyl}-carbamic acid methyl ester

Produkt 1

HCID 11563875(1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-phosphonooxy hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product of step G prepared above (152 mg) was dissolved in anhydrous dichloromethane (3.0 mL). Trimethylsilyl bromide (0.5 mL) was added at 0° C. The mixture was stirred during 1 h at this temperature and overnight at room temperature. The solvent was evaporated and 0.2 mL water was added to the residue. 3 mL EtOH was added mixed and evaporated. This step was repeated three times and the residue dried in vacuo. Yields 98 mg 70% of the title derivatives of this first example.

Aufarbeitung

  1. customThe solvent was evaporated
  2. addition0.2 mL water was added to the residue
  3. addition3 mL EtOH was added
  4. additionmixed
  5. customevaporated
  6. customthe residue dried in vacuo
  7. customYields 98 mg 70% of the title derivatives of this first example

Quellen und Nachweise

ORD-Eintrag
ord-196f3ad9995f4b0da2bdd77d30eb1d4b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227450B2

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