ChemicalBook CAS DataBase List (S)-N-Boc-allylglycine

(S)-N-Boc-allylglycine synthesis

7synthesis methods

Product Name:(S)-N-Boc-allylglycine
CAS Number:90600-20-7
Molecular formula:C10H17NO4
Molecular Weight:215.25

16338-48-0 Synthesis

16338-48-0
238 suppliers
$11.00/250mg

24424-99-5 Synthesis

24424-99-5
811 suppliers
$13.50/25G

90600-20-7
131 suppliers
$15.00/100mg

Yield:90600-20-7 100%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water at 0 - 20; for 18 h;

Steps:

13.1
Stage 1; - (2S)-2-[(fert-Butoxycarbonyl)amino]pent-4-enoic acidTo a solution of (2S)-2-aminopent-4-enoic acid (1.0Og, 8.70mmol) in 1 M NaOH (2OmL) and dioxane (1OmL) at O⁰C was added BOC₂O (2.28g, 10.5mmol). The reaction mixture was allowed to warm to RT and stirred for an additional 18 hours. The pH was checked and adjusted to basic when necessary. The reaction mixture was concentrated under reduced pressure and the aqueous phase washed with Et₂O (2 x 1OmL) to remove the excess BOC₂O. The aqueous phase was acidified to pH2 with 2M H₂SO₄ and extracted with EtOAc (4 x 2OmL) while saturating the aqueous each time with sodium chloride. The combined organic layers were dried (MgSO₄) and concentrated under reduced pressure to afford the product (2.2g, 100% yield). ESMS m/z: 238 [M+Na]⁺.

References:

CHROMA THERAPEUTICS LTD. WO2008/50096, 2008, A1 Location in patent:Page/Page column 50

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