Boc-Dap-OH → HCID 86647135, Verbindung

HRID 2369801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369801
[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:43])[NH:22][CH2:23][C@H:24]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:25]([O:27]N1C(=O)CCC1=O)=O)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)CCCCCCCCCCCCCCC(=O)NCCCC[C@H](NC(OC(C)(C)C)=O)C(ON1C(=O)CCC1=O)=O)(C)(C)C.[NH2:92][CH2:93][C@H:94]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[C:95]([OH:97])=[O:96]>CN(C=O)C>[C:1]([O:5][C:6](=[O:44])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:43])[NH:22][CH2:23][C@H:24]([NH:35][C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[C:25](=[O:27])[NH:92][CH2:93][C@H:94]([NH:98][C:99]([O:101][C:102]([CH3:105])([CH3:104])[CH3:103])=[O:100])[C:95]([OH:97])=[O:96])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 2755946Boc-Dap-OH2×HCID 86647136HCID 86647136, VerbindungHCID 86647137HCID 86647137, Verbindung

Produkt 1

HCID 86647135HCID 86647135, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

15-[(S)-2-tert-Butoxycarbonylamino-2-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)ethylcarbamoyl]pentadecanoic acid tert-butyl ester can be prepared in similar fashion as that described for 15-[(S)-5-tert-butoxycarbonylamino-5-(2,5-dioxopyrrolidin-1-yloxycarbonyl)pentylcarbamoyl]pentadecanoic acid tert-butyl ester using (S)-3-amino-2-tert-butoxycarbonylamino propionic acid, and it can be reacted with (S)-3-amino-2-tert-butoxycarbonylamino propionic acid in DMF at RT for 16 h. After concentrating under vacuum, AcOEt can be added the residue and the mixture can be washed with 0.2 N HCl. The organic phase is then dried over MgSO4 and concentrated under vacuum to yield the crude product, 15-[(S)-2-tert-butoxycarbonylamino-2-((S)-2-tert-butoxycarbonylamino-2-carboxyethylcarbamoyl)ethylcarbamoyl]pentadecanoic acid tert-butyl ester. This can either be used without further purification or purified by flash chromatography.

Aufarbeitung

  1. concentrationAfter concentrating under vacuum, AcOEt
  2. additioncan be added the residue
  3. washthe mixture can be washed with 0.2 N HCl
  4. dry with materialThe organic phase is then dried over MgSO4
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2a437cef76e94a4fb01327df72b71bdf
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710000B2

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