Sodium Hydroxide → 6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

HRID 249629

Reaktionsgleichung

Reaktionsgleichung von HRID 249629
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:24])[CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[OH-].[Na+]>CO>[CH2:17]([O:16][C:14]([NH:13][CH2:12][CH2:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2])=[O:24])=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 692961146-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl ester

Produkt 1

HCID 692965966-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound 36 was prepared using General Procedure A with ester 35 (3.20 g, 9.13 mmol) and an aqueous NaOH solution (1.46 g, 36.53 mmol in 40 mL of H2O) in MeOH (40 mL). Recrystallization from MeOH produced the desired acid 36 in 95% (2.92 g) yield as a white solid. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.10 (s, 1H, NH), 5.67 (s, 1H, NH), 5.04 (s, 2H, OCH2Ar), 3.45 (dt, J=6.4, 12.0 Hz, 2H, CH2NHCO), 3.21 (dt, J=6.4, 12.8 Hz, 2H, CH2NHCO), 2.40 (dt, J=6.0, 6.4 Hz, 2H, CH2CO), 2.32 (t, J=7.2 Hz, 2H, CH2CO), 1.61 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.33 (m, 2H, CH2); ESI-MS m/z 371[M+Cl]−, 359[M+Na]+, 337[M+H]+, 335[M−H]−.

Aufarbeitung

  1. customThe compound 36 was prepared
  2. customRecrystallization from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-54d682a6b1bc444dbeb90db8e1f94eb9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07862807B2

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