ChemicalBook CAS DataBase List N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID

N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID synthesis

10synthesis methods

Product Name:N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID
CAS Number:102507-13-1
Molecular formula:C10H19NO5
Molecular Weight:233.26

Carbamic acid, [(1R)-2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

473545-40-3

N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID

102507-13-1

The general procedure for the synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic acid from tert-butyl (R)-(1,3-dihydroxy-3-methylbutan-2-yl)carbamate was as follows: 2,2,6,6-tetramethylpiperidinium 1-yloxy (TEMPO, 2.3 g, 15 mmol) was added to (R)-(1,3-dihydroxy-3-methyl tert-butyl (33.0 g, 150 mmol) carbamate in acetonitrile (750 mL) and sodium phosphate buffer (600 mL, 0.7 M, pH 6-7) and heated to 35 °C. Subsequently, sodium chlorite solution (34.2 g, dissolved in 150 mL of water) and dilute sodium hypochlorite solution (3 mL of commercial solution diluted in 100 mL of water, 60 drops total) were added dropwise simultaneously to the reaction mixture. The reaction mixture was stirred at 35°C overnight, cooled to room temperature, then the pH was adjusted to 3 with citric acid (~15 g), saturated with sodium chloride, and extracted with ethyl acetate (3 x 2 L). The organic phases were combined and concentrated under reduced pressure. The residue was dissolved in 1.5 L of 2 M sodium carbonate solution and washed with ethyl acetate (2 x 2 L). The aqueous layer was cooled to 0°C, the pH was adjusted to 3.0 with 2M phosphoric acid solution and saturated again with sodium chloride. Extracted with ethyl acetate (3×2L), the organic phases were combined, dried, filtered and concentrated under reduced pressure to give (S)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-methylbutanoic acid (28.4 g, 81% yield) as a colorless solid. NMR (400 MHz, DMSO-d6): δ= 1.15 (s, 3H), 1.17 (s, 3H), 1.39 (s, 9H), 3.86 (d, J = 8.6 Hz, 1H), 6.52 (d, J = 8.9 Hz, 1H).

182958-73-2 Synthesis

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

182958-73-2
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102507-13-1
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Yield:102507-13-1 76%

Reaction Conditions:

with sodium dihydrogenphosphate in tetrahydrofuran at 0; for 4 h;

Steps:

1.2 Step 2: Preparation of (s)-2-tert-butoxyamido-3-methyl-3-hydroxybutyric acid
(s)-2-tert-butoxyamido-3-methyl-3-hydroxybutanol (20 g) was added to THF (50 mL). After adding saturated sodium dihydrogen phosphate solution (50 mL), the reaction was cooled to 0°C. Add bleach (6%, 350 mL) slowly. After 4 hours of reaction, slowly rise to room temperature. After TLC detects that the reaction is complete, it is quenched by adding sodium thiosulfate. Rotary evaporation to remove THF, then add dichloromethane (100mLX4) for extraction, dry and filter, concentrate to the crude reaction product, add n-hexane (100mL), beating and filtering to obtain pure product (s)-2-tert-butoxyamide -3-Methyl-3-hydroxybutyric acid (16 g, 76%).

References:

Zhejiang Kaipu Chemical Co., Ltd.;Luo Linfeng;Tan Xianghui;Yan Xiaodong;Shen Yipeng;Zhou Chen CN111909067, 2020, A Location in patent:Paragraph 0023-0025; 0028-0029

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473545-40-3
25 suppliers
$45.00/10mg

102507-13-1
133 suppliers
$43.00/100mg

References