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Chemical Structure| 75315-60-5 Chemical Structure| 75315-60-5

Structure of 75315-60-5

Chemical Structure| 75315-60-5

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Product Details of [ 75315-60-5 ]

CAS No. :75315-60-5
Formula : C5H9NO3
M.W : 131.13
SMILES Code : O=C(C1(O)CNCC1)O
MDL No. :MFCD19217698

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Application In Synthesis of [ 75315-60-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 75315-60-5 ]

[ 75315-60-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 24424-99-5 ]
  • [ 75315-60-5 ]
  • [ 1067239-08-0 ]
YieldReaction ConditionsOperation in experiment
N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.N-Boc-l-amino-but-3-ene3-Buten-l -amine (4.93 g, 0.069 mol) was submitted to Procedure 7 for Boc protection to yield a crude, which was purified by flash chromatography (silica gel/hexanes: ethyl acetate 0-30%) to yield N-Boc-l-amino-but-3-ene (6.47 g, 0.038 mol, 55.1 % yield).; Step No. 3. Boc protection: To a stirring solution of solid from step No.2 in2 M NaOH (20 mL) and i-PrOH (20 mL) at 0C was added BoC2O (6.6 g, 3 mmol) in small portions, and the reaction mixture was allowed to warm to room temperature over4 h. i-PrOH was then evaporated, and H2O (50 mL) was added, and the aqueous phase was separated and extracted with Et2O (2 x 30 ml). The aqueous layer was acidified to pH 3 by addition of dilute H3PO4 and was extracted with EtOAc (2 x 60 ml). The combined organic layers were washed with H2O (2 x 30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated to yield the desired N-Boc-alpha-hydroxy carboxylic acids in 56-72% yield.
With sodium hydroxide; In isopropyl alcohol; at 0 - 20℃; N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-3 -hydroxy-pyrrolidine-3 -carboxylic acid.
With sodium hydroxide; In water; isopropyl alcohol; at 0 - 20℃; for 4h; Step No. 3. Boc protection: To a stirring solution of solid from step No.2 in2 M NaOH (20 mL) and i-PrOH (20 mL) at 00C was added BoC2O (6.6 g, 3 mmol) in small portions, and the reaction mixture was allowed to warm to room temperature over 4 h. i-PrOH was then evaporated, and H2O (50 mL) was added, and the aqueous phase was separated and extracted with Et2O (2 x 30 ml). The aqueous layer was acidified to pH 3 by addition of dilute H3PO4 and was extracted with EtOAc (2 x 60 ml). The combined organic layers were washed with H2O (2 x 30 mL) and brine (30 mL), dried <n="46"/>over Na2SO4, filtered and concentrated to yield the desired N-Boc-alpha-hydroxy carboxylic acids in 56-72% yield. Example 34 6'-(2-Hydroxy-ethyl)-l-(3-hydroxy-pyrrolidin-3-yl-acetyl)-sisomicinN-Boc-S-hydroxypyrrolidine-S-carboxylic acidN-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 15 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid.
N-Boc-3-pyrrolidone (0.010 mmol) was submitted to Procedure 9 to yield the desired N-Boc-S-hydroxy-pyrrolidine-S-carboxylic acid..; Step No. 3. Boc protection: To a stirring solution of solid from step No.2 in2 M NaOH (20 mL) and i-PrOH (20 mL) at 0C was added BoC2O (6.6 g, 3 mmol) in small portions, and the reaction mixture was allowed to warm to room temperature over4 h. i-PrOH was then evaporated, and H2O (50 mL) was added, and the aqueous phase was separated and extracted with Et2O (2 x 30 ml). The aqueous layer was acidified to pH 3 by addition of dilute H3PO4 and was extracted with EtOAc (2 x 60 ml). The combined organic layers were washed with H2O (2 x 30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated to yield the desired N-Boc-alpha-hydroxy carboxylic acids in 56-72% yield.

 

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