Bromotrimethylsilane → (S)-7-[[Hydroxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

HRID 1156813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156813
C([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[CH2:26][C:21]2([S:25][CH2:24][CH2:23][S:22]2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])C.Br[Si](C)(C)C>ClCCl>[OH:5][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:29])[CH2:26][C:21]2([S:22][CH2:23][CH2:24][S:25]2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:3]

Komponenten

4

Edukt 2

HCID 76113BromotrimethylsilaneHCID 86738447(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

Produkt 1

HCID 13326552(S)-7-[[Hydroxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl esterAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester (3.4 g) in dry dichloromethane is treated with bromotrimethylsilane (1.5 ml) under argon at room temperature. After 3 hours the dichloromethane and excess bromotrimethylsilane are removed in vacuo and the residue taken up in water and ethyl acetate and stirred for 5 minutes. The layers are separated and the organic phase is washed with brine and dried (MgSO4). The solvent is stripped yielding 3.3 g of the title compound as a foam.

Aufarbeitung

  1. customAfter 3 hours the dichloromethane and excess bromotrimethylsilane are removed in vacuo
  2. customThe layers are separated
  3. washthe organic phase is washed with brine
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-9d49b693131b44809fcfb255fbd5d0a1
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04337201

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