Water → trans-(R)-3-(4-(((4-tert-butylcyclohexyl)(1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)benzamido)-2-hydroxypropanoic acid

HRID 229991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229991
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:38]=[CH:37][C:26]([C:27]([NH:29][CH2:30][C@@H:31]([OH:36])[C:32]([O:34]C)=[O:33])=[O:28])=[CH:25][CH:24]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].O>CO>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][CH2:30][C@@H:31]([OH:36])[C:32]([OH:34])=[O:33])=[O:28])=[CH:37][CH:38]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 57758784Methyl (2r)-3-[(4-{[(4-tert-butylcyclohexyl)(1-methyl-1h-benzimidazol-2-yl)amino]-methyl}benzoyl)amino]-2-hydroxypropanoate

Produkt 1

HCID 44561584trans-(R)-3-(4-(((4-tert-butylcyclohexyl)(1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)benzamido)-2-hydroxypropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of the title compound of Example 7 (0.1 mmol, 50 mg) in 2 mL of MeOH was added LiOH (0.5 mmol, 12 mg). H2O was added dropwise until the reaction became slightly cloudy, then the mixture was sonicated to dissolve the LiOH. The reaction was stirred at 40° C. for 2 h. The reaction was concentrated under reduced pressure and the residue was taken up in dioxane/H2O and acidified with TFA. Purification by reverse-phase HPLC (Condition A), followed by lyophilization, afforded the title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.79 (d, 2H), 7.58 (m, 1H), 7.39-7.52 (overlapping m, 5H), 4.86 (s, 2H), 4.34 (m, 1H), 3.87 (s, 3H), 3.52-3.84 (overlapping m, 3H), 2.16 (m, 2H), 1.99 (m, 2H), 1.84 (m, 2H), 1.31 (m, 2H), 1.14 (m, 1H), 0.92 (s, 9H). MS (ESI): m/z 487 (M+H). MS (ESI): m/z 507 (M+H). HPLC A: 1.84 min.

Aufarbeitung

  1. customthe mixture was sonicated
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customPurification by reverse-phase HPLC (Condition A),

Quellen und Nachweise

ORD-Eintrag
ord-897a23569364414a96b2ee13a0139ec2
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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