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Sodium Bicarbonate → S-Ethyl O-(N3,N7,N12,N16-tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoyl oxy)methyl carbonothioate

HRID 1397113
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1397113
[C:1](=[O:8])([O:5][CH2:6]I)[S:2][CH2:3][CH3:4].[C:9]([O:13][C:14]([N:16]([CH2:21][CH2:22][CH2:23][N:24]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:25][CH2:26][CH2:27][CH2:28][N:29]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:17][C:18]([OH:20])=[O:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])(O)=O.[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O.C(Cl)Cl>[C:1](=[O:8])([O:5][CH2:6][O:20][C:18](=[O:19])[CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:21][CH2:22][CH2:23][N:24]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:25][CH2:26][CH2:27][CH2:28][N:29]([C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])[CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[S:2][CH2:3][CH3:4]
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Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 11006845N3,N7,N12,N16-Tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoic acidHCID 11436522(Ethylsulfanyl)(iodomethoxy)methanone

Produkt 1

HCID 86666527S-Ethyl O-(N3,N7,N12,N16-tetra(t-butoxycarbonyl)-3,7,12,16-tetraazahexadecanoyl oxy)methyl carbonothioateAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433
Tetrabutylammonium hydrogen sulfate
Katalysator
HCID 6344DichloromethaneLösungsmittel
HCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

S-Ethyl O-iodomethyl carbonothioate (423 mg, 1.72 mmol) was added to a stirring mixture of 31 (1.13 g, 1.71 mmol), NaHCO3 (298 mg, 3.55 mmol) and tetrabutylammonium hydrogensulfate (588 mg, 1.73 mmol) in CH2Cl2/H2O (1:1, 17 mL) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (80 mL) and the aqueous layer was discarded. The organic layer was washed with saturated aqueous NH4Cl, saturated aqueous NaCl, dried over Na2SO4 then concentrated under reduced pressure. The residue was resuspended in Et2O, filtered and again concentrated under reduced pressure. The crude material was purified by silica gel chromatography (25%-60% EtOAc in hexanes over 10 column volumes) to give the colourless liquid 32 (1.23 g, 92%): 1H NMR (400 MHz, CDCl3): δ 1.32 (t, J=7.3, 3H), 1.41-1.47 (m, 40H), 1.61-1.75 (m, 4H), 2.89 (q, J=7.3, 2H), 3.10-3.31 (m, 12H), 3.92 (s, 4/7 of 2H, rotamer A), 4.01 (s, 3/7 of 2H, rotomer B), 5.84 (s, 2H).

Aufarbeitung

  1. washThe organic layer was washed with saturated aqueous NH4Cl, saturated aqueous NaCl
  2. dry with materialdried over Na2SO4
  3. concentrationthen concentrated under reduced pressure
  4. filtrationfiltered
  5. concentrationagain concentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography (25%-60% EtOAc in hexanes over 10 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-ef97f8d2e01b45db82fa8cc2c8a27706
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901072B2

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