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Formic Acid → N-(tert-Butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)-ethyl]amino}butyl]carbamoyl}-L-tyrosine

HRID 630678
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 630678
C([O:4][C:5](=[O:62])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:61])[NH:24][CH2:25][CH2:26][C@H:27]([NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[C:28](=[O:52])[NH:29][CH2:30][CH2:31][S:32][C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:18][CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])C=C.C(N(CC)CC)C.C(O)=O>O1CCCC1.O>[C:11]([O:10][C:8]([NH:7][C@H:6]([C:5]([OH:62])=[O:4])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:61])[NH:24][CH2:25][CH2:26][C@H:27]([NH:53][C:54]([O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[O:55])[C:28](=[O:52])[NH:29][CH2:30][CH2:31][S:32][C:33]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:12])([CH3:13])[CH3:14]
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Komponenten

6

Edukt 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 117893244Allyl-N-(tert-butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)ethyl]amino}butyl]carbamoyl}-L-tyrosinate

Produkt 1

HCID 71557574N-(tert-Butoxycarbonyl)-O-{[(3S)-3-[(tert-butoxycarbonyl)amino]-4-oxo-4-{[2-(tritylsulfanyl)-ethyl]amino}butyl]carbamoyl}-L-tyrosine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

98 mg (0.1 mmol) of the compound from example 15A was dissolved in approx. 4 ml tetrahydrofuran. 70 μl (0.5 mmol) Triethylamine, 19 μl (0.5 mmol) formic acid and 11 mg (0.01 mmol) tetrakis(triphenylphosphin)palladium(0) were added. The reaction mixture was stirred over night at room temperature. The reaction was diluted with approx. 5 ml water and twice extracted with approx. 5 ml dichloromethane. The combined organic phases were extracted with brine, dried over sodium sulfate and concentrated to dryness under reduced pressure. The raw product was purified by preparative RP-HPLC on a C18 column with a water/methanol gradient to yield 67 mg (79% of theory) product.

Aufarbeitung

  1. extractiontwice extracted with approx. 5 ml dichloromethane
  2. extractionThe combined organic phases were extracted with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe raw product was purified by preparative RP-HPLC on a C18 column with a water/methanol gradient
  6. customto yield 67 mg (79% of theory) product

Quellen und Nachweise

ORD-Eintrag
ord-7452d2bea8304b4488fdc607a81c73c0
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315543B2

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