CBZ-ALPHA-ALLYL-L-GLY synthesis
- Product Name:CBZ-ALPHA-ALLYL-L-GLY
- CAS Number:78553-51-2
- Molecular formula:C13H15NO4
- Molecular Weight:249.26
13139-17-8
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16338-48-0
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78553-51-2
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Yield:78553-51-2 100%
Reaction Conditions:
with water;triethylamine in 1,4-dioxane;
Steps:
2.a a. (2S)-2-{ F (BENZYLOXY) CARBONVLLAMINOLPENT-4-ENOIC acid (2a)
To a suspension of L-2-amino-4-pentenoic acid (2.0 g) in Dioxane (80 mL) at RT was added triethylamine (4. 3 g), water (2.0 mL), and N- (BENZYLOXYCARBONYLOXY) succinimide (9.1 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NaHCO3 and extracted with ether (3x). The basic aqueous layer was acidified to pH 2 with 2N HCl and extracted with EtOAc (3x). The combined EtOAc layer was washed with brine, dried (NA2S04), filtered and evaporated, then concentrated from Toluene (2x) to give a viscous oil (4. 51 g, QUANTITATIVE). LH NMR (300 MHz, DMSO-d6) 6 2.31-2. 50 (M, 2H), 4. 00-4. 06 (m, 1H), 5.03 (s, 2H), 5.05-5. 12 (m, 2H), 5.71-5. 84 (m, 1H), 7.35 (M, 5H), 7.53 (d, 1H), 12.57 (bs, 1H). MS APCI, m/z = 250 (M+1). LC/MS 2.30 min. , Method A.
References:
WO2004/80983,2004,A1 Location in patent:Page 47
16338-48-0
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501-53-1
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78553-51-2
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50299-14-4
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501-53-1
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121786-40-1
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78553-51-2
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149117-86-2
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50299-14-4
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78553-51-2
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26054-60-4
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3536-96-7
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78553-51-2
59 suppliers
$36.00/100mg