ChemicalBook CAS DataBase List Boc-3-Hydroxy-1-adamantyl-D-glycine

Boc-3-Hydroxy-1-adamantyl-D-glycine synthesis

7synthesis methods

Product Name:Boc-3-Hydroxy-1-adamantyl-D-glycine
CAS Number:361442-00-4
Molecular formula:C17H27NO5
Molecular Weight:325.4

361441-97-6 Synthesis

361441-97-6
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$120.00/250mg

361442-00-4
321 suppliers
$8.00/250mg

Tricyclo[3.3.1.13,7]decane-1-acetic acid, α-[[(1,1-diMethylethoxy)carbonyl]aMino]-3,5-dihydroxy-, (αS)-

681282-72-4
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Yield:361442-00-4 51% ，681282-72-4 17%

Reaction Conditions:

with potassium hydroxide;potassium permanganate in water at 60 - 90; for 1.5 h;

Steps:

1.8

A SOLUTION OF KMN04 (337 mg, 2.13 mmol, 1.1 equiv) in 2% aq KOH (6 mL) was heated to 60°C and Step 7 compound in general method G (600 mg, 1.94 mmol, 1 equiv) was added in portions, and heating increased to 90°C. After 1.5 h, the reaction was cooled to 0°C, EtOAc (50 mL) was added, and the mixture was carefully acidified to pH 3 with 1 N HCI. The layers were separated and the aqueous was extracted with EtOAc (50 mL). The combined organic extracts were washed with brine, dried over NA2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (3. 8x15 cm) with 2% (200 mL), 3% (200 mL), 4% (200 mL), and 5% (500 mL) MEOH/CH2CI2 + 0.5% HOAc. After isolation of the product, the material was chased with hexanes to afford a white solid (324 mg, 51 %) : MS M/E 326 (m+H) +. Refer to the procedure of Example 1, Step 8 that generates HYDROXYADAMANTYL-N-TERT- butyloxycarbonyl-L-glycine. During the reaction, the DIOI is formed as a lower Rf minor product. Slightly longer reaction times (up to 90 min) gave up to 17% of the diol in addition to the Example 1, Step 8 compound. With the procedure identical in every other respect, the diol is obtained as a white solid, after chasing with hexanes, by flushing the column with 15% MEOH-CH2CI2-0. 5% HOAC. 1H NMR (500 MHz, CD30D) 1.41-1. 73 (m, 21 H), 2.29 (BRS, 1H), 3.95 (s, 1H). 13C NMR (125 MHz, CD30D) 174.2, 157.9, 80.6, 71.0, 70.9, 63.1, 52.5, 49.6, 48.3, 46.3, 43.9, 41.8, 37.5, 31. 8, 28.7.

References:

WO2005/12249,2005,A2 Location in patent:Page/Page column 36-37

361441-97-6 Synthesis

361441-97-6
113 suppliers
$120.00/250mg

361442-00-4
321 suppliers
$8.00/250mg

References