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1,2-Dichloroethane → 7-(2-(((1,1-Dimethylethoxy)carbonyl)amino)-1-oxo-3-((triphenylmethyl)thio)-propyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

HRID 639424
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 639424
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]2[CH:16]([CH2:17][CH2:18][S:19][C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:15][CH2:14][CH2:13][N:12]2[CH:39]=1.[NH:40]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[C@H:41]([C:63](O)=[O:64])[CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1>[CH3:71][C:69]([CH3:72])([O:68][C:66]([NH:40][CH:41]([CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:63]([N:15]1[CH2:14][CH2:13][N:12]2[CH:39]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:10]=[C:11]2[CH:16]1[CH2:17][CH2:18][S:19][C:20]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:64])=[O:67])[CH3:70]
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Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 11167161N-((1,1-Dimethylethoxy)carbonyl)-S-(triphenylmethyl)-L-cysteineHCID 220168072-(2-Methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine

Produkt 1

HCID 22016823
7-(2-(((1,1-Dimethylethoxy)carbonyl)amino)-1-oxo-3-((triphenylmethyl)thio)-propyl)-2-(2-methoxyphenyl)-5,6,7,8-tetrahydro-8-(2-((triphenylmethyl)thio)ethyl)-imidazo[1,2-a]pyrazine
Ausbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of the product from Step 13.g. (compound xxi, where R2, R3, R5, R6, and R7 are H, R4 is 2-methoxyphenyl, and n is 1) (1.30 g, 2.45 mmol), Boc-(L)-Cys(Trt)-OH (1.14 g, 2.45 mmol), NMM (270 uL, 2.45 mmol), and HOAt (333 mg, 2.45 mmol) in THF (20 ml) was treated with EDC (470 mg, 2.45 mmol) at room temperature under N2. The reaction was stirred overnight and then concentrated under reduced pressure. Saturated NaHCO3 solution (25 ml) was added and the product was extracted with a 3:2 mixture of hexanes:EtOAc. The extracts were applied to a silica gel column and the product was eluted with 3:2/hexanes:EtOAc. Product fractions were combined and concentrated under reduced pressure to obtain a white foam (2.31 g, 97%) which was used without further purification. Mass spec. 977.6 MH+.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionSaturated NaHCO3 solution (25 ml) was added
  3. extractionthe product was extracted with a 3:2 mixture of hexanes
  4. washthe product was eluted with 3:2/hexanes
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-31316370bd7249d1abefec25d45db2af
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691859B2

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