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[ CAS No. 88050-17-3 ] {[proInfo.proName]}

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Chemical Structure| 88050-17-3
Chemical Structure| 88050-17-3
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Product Details of [ 88050-17-3 ]

CAS No. :88050-17-3 MDL No. :MFCD00151929
Formula : C20H19NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :GOUUPUICWUFXPM-XIKOKIGWSA-N
M.W :353.37 Pubchem ID :2756109
Synonyms :

Safety of [ 88050-17-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 88050-17-3 ]

* 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.

  • Upstream synthesis route of [ 88050-17-3 ]
  • Downstream synthetic route of [ 88050-17-3 ]

[ 88050-17-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 67-56-1 ]
  • [ 88050-17-3 ]
  • [ 122350-59-8 ]
Reference: [1] Journal of Fluorine Chemistry, 1997, vol. 82, # 2, p. 125 - 130
  • 2
  • [ 28920-43-6 ]
  • [ 51-35-4 ]
  • [ 88050-17-3 ]
YieldReaction ConditionsOperation in experiment
150 g With sodium hydrogencarbonate In tetrahydrofuran; water at 25 - 30℃; Example 2
Synthesis of (2S, 4R)-1-[(9H-fluoren-9-ylmethoxy) carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
To a solution of (2S,4R)-4-hydroxy-L-proline (100 g) in tetrahydrofuran (200 ml) was added sodium bicarbonate (80 g), water (400 ml) and 9-fluorenylmethyloxycarbonyl (Fmoc) chloride (226 g) solution (in 200 ml THF) at 25-30° C.
The reaction mixture was stirred at about 25-30° C. for about 10-12 h.
After completion of reaction, water was added.
Then the aq.
reaction mass was washed with diisopropyl ether (DIPE) and acidified with 1N hydrochloric acid.
The reaction mixture was stirred for about 2-3 hours.
The solid was collected by filtration to give the 150 g of title compound as white solid.
1H NMR (300 MHz, DMSO-d6): δ 1.89-2.24 (m, 2H), 3.34-3.43 (m, 2H), 3:43-3.54 (m, 0.5H), 4.12-4.21 (m, 3H), 4.25 (s, 2H), 4.28-4.42 (m, 0.5H), 5.16 (brs, 1H), 7.29-7.34 (m, 2H), 7.38-7.65 (m, 21-1), 7.63-7.65 (m, 2H), 7.87-7.89 (m, 2H)
Melting point:-188-190° C.
Mass-(M+H):-354.33
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 51, p. 9509 - 9512
[2] Angewandte Chemie - International Edition, 2009, vol. 48, # 10, p. 1784 - 1787
[3] Patent: US9518048, 2016, B2, . Location in patent: Page/Page column 24
  • 3
  • [ 51-35-4 ]
  • [ 88050-17-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In 1,4-dioxane; water; toluene Example 89
N-Fmoc-4R-Hydroxy-L-Proline
trans-4-Hydroxy-L-proline (5.00 g, 38.2 mmol) and NaHCO3 (8.00 g, 95.2 mmol) were suspended in 150 ml H2O/Dioxane (1:1).
Fluorenylmethyl chloroformate (11.4 g, 44.0 mmol) in 25 ml toluene was added dropwise.
The temperature of the reaction was not allowed to rise above 25° C. during the addition.
The mixture was stirred vigorously overnight, and then quenched with 50 ml saturated NaHCO3 solution and 50 ml water.
The solution was then extracted with 100 ml diethyl ether.
The aqueous layer was acidified to pH 1 with concentrated HCl, and extracted twice with ethyl acetate, and the organic extracts washed with brine.
The solution was dried with MgSO4, filtered and the solvent removed in vacuo.
The pure product crystallized from the concentrated solution. Yield: 13.4 g (100percent).
1H NMR: (CDCl3, 200 MHz) δ7.75-7.15 (8H, m, ArH), 4.55-4.05 (5H, m, ArCHCH2, H2, H4), 3.65-3.45 (2H, m, 2 H5), 2.35-2.10 (2H, m, 2 H3).
100% With sodium hydrogencarbonate In 1,4-dioxane; water; toluene EXAMPLE 1
N-Fmoc-trans-4-Hydroxy-L-Proline
trans-4-Hydroxy-L-proline (5.00 g, 38.2 mmol) and NaHCO3 (8.00 g, 95.2 mmol) were suspended in 150 ml H2 O/Dioxane (1:1).
Fluorenylmethyl chloroformate (11.4 g, 44.0 mmol) in 25 ml toluene was added dropwise.
The temperature of the reaction was not allowed to rise above 25° C. during the addition.
The mixture was stirred vigorously overnight, and then quenched with 50 ml saturated NaHCO3 solution and 50 ml water.
The solution was then extracted with 100 ml diethyl ether.
The aqueous layer was acidified to pH 1 with concentrated HCl, and extracted twice with ethyl acetate, and the organic extracts washed with brine.
The solution was dried with MgSO4, filtered and the solvent removed in vacuo.
The pure product crystallized from the concentrated solution. Yield: 13.4 g (100percent).
1 H NMR: (CDCl3, 200 MHz) δ 7.75-7.15 (8H, m, ArH), 4.55-4.05 (5H, m, ArCHCH2, H2, H4), 3.65-3.45 (2H, m, 2 H5), 2.35-2.10 (2H, m, 2 H3).
100% With sodium hydrogencarbonate In 1,4-dioxane; water; toluene EXAMPLE 1
N-Fmoc-trans-4-Hydroxy-L-Proline
trans-4-Hydroxy-L-proline (5.00 g, 38.2 mmol) and NaHCO3 (8.00 g, 95.2 mmol) were suspended in 150 ml H2O/Dioxane (1:1).
Fluorenylmethyl chloroformate (11.4 g, 44.0 mmol) in 25 ml toluene was added dropwise.
The temperature of the reaction was not allowed to rise above 25° C. during the addition.
The mixture was stirred vigorously overnight, and then quenched with 50 ml saturated NaHCO3 solution and 50 ml water.
The solution was then extracted with 100 ml diethyl ether.
The aqueous layer was acidified to pH 1 with concentrated HCl, and extracted twice with ethyl acetate, and the organic extracts washed with brine.
The solution was dried with MgSO4, filtered and the solvent removed in vacuo.
The pure product crystallized from the concentrated solution. Yield: 13.4 g (100percent).
1H NMR: (CDCl3, 200 MHz) δ 7.75-7.15 (8H, m, ArH), 4.55-4.05 (5H, m, ArCHCH2, H2, H4), 3.65-3.45 (2H, m, 2 H5), 2.35-2.10 (2H, m, 2 H3).
Reference: [1] Patent: US6316626, 2001, B1,
[2] Patent: US5714606, 1998, A,
[3] Patent: US6828427, 2004, B1,
[4] Patent: US6184389, 2001, B2,
  • 4
  • [ 82911-69-1 ]
  • [ 88050-17-3 ]
Reference: [1] Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 183 - 186
  • 5
  • [ 7536-89-2 ]
  • [ 88050-17-3 ]
Reference: [1] Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 183 - 186
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