Z-1-NAL-OH synthesis
- Product Name:Z-1-NAL-OH
- CAS Number:65365-15-3
- Molecular formula:C21H19NO4
- Molecular Weight:349.38
55516-54-6
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501-53-1
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65365-15-3
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Yield:65365-15-3 89%
Reaction Conditions:
with sodium hydroxide in tetrahydrofuran at 0 - 20; for 2 h;
Steps:
(S)-2-(((benzyloxy)carbonyl)amino)-3-(naphthalen-1-yl)propanoic acid
(S)-2-(((benzyloxy)carbonyl)amino)-3-(naphthalen-1-yl)propanoic acid
Benzyl carbonochloridate (1.081 mL, 7.67 mmol) and NaOH (8.36 mL, 8.36 mmol) were dropped at the same time to a stirred solution of (S)-2-amino-3-(naphthalen-1-yl)propanoic acid (1.5 g, 6.97 mmol) in THF (7 mL) and 7 ml of 1N NaOH at 0° C.
The mixtures were allowed to stir at RT for 2 hours at which time LC-MS showed desired product peak Acidified with 1N HCl and extracted with EtOAc.
Removed EtOAc and the obtained crude materials were purified by RediSep Column: Silica 80 g
Flow Rate: 60 ml/min.
Solvent: A dichloromethane; Solvent: B 20% MeOH/80% DCM.
Gradient 0%-50% SolB in 20 mins.
Fractions containing the desired product were combined and dried via centrifugal evaporation to provide the title compound (2.21 g, 89%).
Analysis LCMS Condition A: Retention time=0.98 min; ESI-MS(+) m/z 350.08 (M+H).
References:
US2016/222060,2016,A1 Location in patent:Paragraph 0480; 0481; 0482; 0483; 0484; 0485; 0486
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65365-15-3
50 suppliers
$104.38/250MG