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Formic Acid → Boc-Leu-Leu-Lys(Z)-Leu-Leu-OH

HRID 849691
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 849691
[OH-].[Na+].[NH:3]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:4]([C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:52]([O:54]C)=[O:53])[CH2:48][CH:49]([CH3:51])[CH3:50])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH2:5][CH:6]([CH3:8])[CH3:7].C1COCC1.C(O)=O>O.C(OCC)(=O)C>[NH:3]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:4]([C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:52]([OH:54])=[O:53])[CH2:48][CH:49]([CH3:50])[CH3:51])=[O:45])[CH2:40][CH:41]([CH3:42])[CH3:43])=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH2:5][CH:6]([CH3:8])[CH3:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12020547Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe

Produkt 1

HCID 12020548Boc-Leu-Leu-Lys(Z)-Leu-Leu-OHAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

A solution of NaOH(1.44 g, 36.0 mmol) in H2O (15.0 g) was added at 20-25° C. over 5 min to a mixture of Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe (SEQ. ID No. 2) (12.0 g, 14.16 mmol) THF (48.0 g) and H2O (18.0 g). The resulting mixture was stirred for 2 h. 98% Formic acid (5 g) was added, followed by ethyl acetate (30.0 g). The resulting organic phase was washed with H2O, concentrated in vacuo and the residue was dissolved in MeOH (60.0 g). The solids were filtered and rinsed with an additional portion of MeOH (8.0 g). The combined MeOH solution was heated to 60-65° C. and H2O (30.0 g) was added over 10 min. This mixture was cooled to 20-25° C., the solid product began to crystallize. An additional portion of H2O (35.0 g) was added and the mixture was stirred for 1 h. The solid product was filtered, washed with H2O and dried in vacuo to give Boc-Leu-Leu-Lys(Z)-Leu-Leu-OH (SEQ. ID No. 2) (11.5 g, 97.5%).

Aufarbeitung

  1. washThe resulting organic phase was washed with H2O
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was dissolved in MeOH (60.0 g)
  4. filtrationThe solids were filtered
  5. washrinsed with an additional portion of MeOH (8.0 g)
  6. additionH2O (30.0 g) was added over 10 min
  7. temperatureThis mixture was cooled to 20-25° C.
  8. customto crystallize
  9. additionAn additional portion of H2O (35.0 g) was added
  10. stirringthe mixture was stirred for 1 h
  11. filtrationThe solid product was filtered
  12. washwashed with H2O
  13. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e1e18bdc795742cda2deaf229287bee9
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06013764

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