Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate synthesis
- Product Name:Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate
- CAS Number:124605-42-1
- Molecular formula:C15H21NO5
- Molecular Weight:295.33
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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Yield: 99%
Reaction Conditions:
with hydrogen;1% Pd/C in methanol under 4654.46 Torr;
Steps:
24
Example 24. Methyl (2/?,3S)-2-hydroxy-3-fert-butoxy-carbonylamino-3- phenylpropanoate (33).; To a solution of methyl (2R,3S)-2-benzyloxy-3-te/t- butoxy-carbonylamino-3-phenylpropanoate (32; 55 mg, 0.14 mmol) in MeOH (4 ml_), palladium on carbon (5 mg) was added. The reaction mixture was stirred under H2 (90 psi) atmosphere. When the starting material could no longer be detected by TLC, the solution was filtered through celite and concentrated to give the title compound as white crystals in 99% yield (42 mg). 1H NMR (400 MHz, CDCI3): δ = 7.38-7.18 (m, 5H), 5.44 (d, J=9.6Hz, 1 H), 5.22 (d, J=8.8Hz, 1 H), 4.46 (bs, 1 H), 3.83 (s, 3H), 1.40 (s, 9H); 13C NMR (100 MHz, CDCI3): 173.6, 155.4, 139.3, 128.8, 128.0, 126.9, 80.2, 73.8, 56.3, 53.3, 28.5; HRMS (ESI): calcd for [M+Na] (Ci5H2iNO5) requires m/z 318.1312, found 318.1313; [α]D = + 13.2 (c=1.0, CHCI3).
References:
ORGANOCLICK AKTIEBOLAG;CORDOVA, Armando;DZIEDZIC, Pawel;VESELY, Jan WO2010/24762, 2010, A1 Location in patent:Page/Page column 19-20
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67-56-1
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132201-32-2
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124605-42-1
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24424-99-5
823 suppliers
$13.50/25G
124605-42-1
171 suppliers
$8.00/250mg