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Formic Acid → N-(tert-Butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosine

HRID 630677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 630677
C([O:4][C:5](=[O:65])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[O:64])[NH:24][C@@H:25]([CH2:54][CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[C:26](=[O:53])[NH:27][C@H:28]([C:50](=[O:52])[NH2:51])[CH2:29][S:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([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)=[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:65])=[O:4])[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23](=[O:64])[NH:24][C@@H:25]([CH2:54][CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:62])[CH3:61])[C:26](=[O:53])[NH:27][C@H:28]([C:50](=[O:52])[NH2:51])[CH2:29][S:30][C: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)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][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 89555014Allyl-N-(tert-butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosinate

Produkt 1

HCID 71557416N-(tert-Butoxycarbonyl)-O-{[(4R,7S)-4-carbamoyl-13,13-dimethyl-6,11-dioxo-1,1,1-triphenyl-12-oxa-2-thia-5,10-diazatetradecan-7-yl]carbamoyl}-L-tyrosine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.91 g (5.40 mmol) of the compound from example 14A was dissolved in approx. 110 ml tetrahydrofuran. 3.8 ml (27 mmol) Triethylamine, 1.02 ml (27 mmol) formic acid and 0.62 g (0.54 mmol) tetrakis(triphenylphosphin)palladium(0) were added. The reaction mixture was stirred over night at room temperature. The reaction was diluted with approx. 60 ml water and twice extracted with approx. 50 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 dissolved in dichloromethane and chromatographed over approx. 500 ml silica gel. Solvents used were dichloromethane, dichloromethane/methanol 40/1 and dichloromethane/methanol 1/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. The raw product was further purified by preparative RP-HPLC on a C18 column with a water/methanol gradient to yield 1.96 g (42% of theory) product.

Aufarbeitung

  1. extractiontwice extracted with approx. 50 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. dissolutionThe raw product was dissolved in dichloromethane
  6. customchromatographed over approx. 500 ml silica gel
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe raw product was further purified by preparative RP-HPLC on a C18 column with a water/methanol gradient
  9. customto yield 1.96 g (42% of theory) product

Quellen und Nachweise

ORD-Eintrag
ord-c29f398dcfe64ab0aa2fd3c1bc7de992
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315543B2

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