[ CAS No. 437655-95-3 ]

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Product Details

CAS No. :437655-95-3MDL No. :MFCD26142981
Formula :C25H31NO8InChI Key :XPNLDOFYRFOXLR-UHFFFAOYSA-N
M.W :473.52Pubchem ID :66615355
Boiling Point :-
Synonyms :

Computed Properties

TPSA : 113 H-Bond Acceptor Count : 8
XLogP3 : 2.1 H-Bond Donor Count : 2
SP3 : 0.44 Rotatable Bond Count : 17

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 437655-95-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 195071-49-9 ]
  • [ 102774-86-7 ]
  • [ 437655-95-3 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With potassium carbonate In water at 20℃; for 0.25 h;
Stage #2: for 24.00 h;
L1 (0.79 g, 3.14 mmol) and K2CO3 (1.04 g, 7.50 mmol) were dissolved in 5.8 mL of water and stirred at room temperature for 15 minutes after which N-(9-fluorenylmethoxycarbonyl) succinimide (Fmoc-OSu, 1.28 g, 3.79 mmol) was added and the mixture was stirred for 24 hours, while the progress of the reaction was monitored by TLC (CHCl3/MeOH/AcOH, 5:1:0.06). The salt was filtered and the filtrate was washed with Et2O, acidified to pH 1 using 3 N HCl, and the desired compound extracted with DCM. After removing the solvent in vacuo, Purification by RP-HPLC, the product-containing fraction was lyophilized to give Compound 11a (1.08 g, yield 73percent). Chemical formula of Compound 11a: C25H1NO8 required [M+H]+=474.2, found [M+H]+=474.9, [M+Na]+=496.9.
Reference: [1] Patent: US2018/169262, 2018, A1. Location in patent: Paragraph 0181-0183
  • 2
  • [ 894427-95-3 ]
  • [ 437655-95-3 ]
YieldReaction ConditionsOperation in experiment
67% With trifluoroacetic acid In dichloromethane for 1.50 h; Compound 6 was dissolved in DCM (3.5 mL) and TFA (3.5 mL) was added under a nitrogen atmosphere. After 1.5 h of stirring the reaction mixture was concentrated under reduced pressure. Then the excess of TFA was removed by repeated concentration in toluene. DCM/Et2O (100 mL, 1/2, v/v) was added and washed with 1 N HCl. The water layer was extracted with DCM/Et2O (100 mL, 1/2, v/v). The combined organic layers were washed with brine and dried over MgSO4. After filtration the solvent was removed under atmospheric pressure (50°C). The crude oil was purified by silica column chromatography (DCM/MeOH/AcOH, 99/0/1^89/10/1, v/v/v), to give compound 7. Remaining AcOH was removed by dissolving the crude oily product in DCM/Et2O (1/2, v/v) and washing with H2O (3 times) and brine followed by drying over MgSO4. After filtration the solvent was removed under atmospheric pressure (50°C) to give compound 7 as a yellowish oil (0.37 g, 67percent). Rf 0.32 (DCM/MeOH, 89/10/1, v/v).
67% With trifluoroacetic acid In dichloromethane for 1.50 h; EXAMPLE 215-λr-(9-FluorenyImethyIoxycarbonyl)-15-aza-3,6,9,12-tetraoxa-pentadecanoate (3) Compound 2 was dissolved in DCM (3.5 mL) and TFA (3.5 mL) was added under a nitrogen atmosphere. After 1.5 h of stirring the reaction mixture was concentrated under reduced pressure. Then the excess of TFA was removed by repeated concentration in toluene. DCM/Et2O (100 mL, 1/2, v/v) was added and the solution was washed with 1 N HCl. The water layer was extracted with DCMZEt2O (100 mL, 1/2, v/v). The combined organic layers were washed with brine and dried over MgSO,*. After filtration the solvent was removed under atmospheric pressure (5O0C). The crude oil was purified by silica gel column chromatography (DCM/MeOH/AcOH, 99/0/1^89/10/1, v/v/v), to give compound 3. Remaining AcOH was removed by dissolving the crude oily product in DCMZEt2O (1/2, v/v) and rinsing with H2O (3x) and brine followed by drying over MgSO4. After filtration the solvent was removed under EPO atmospheric pressure (5O0C) to give compound 3 as a yellowish oil (0.37 g, 67percent). Rf 0.32 (DCM/MeOH/AcOH, 89/10/1, v/v).
Reference: [1] Patent: WO2006/67173, 2006, A2. Location in patent: Page/Page column 17; 20
[2] Patent: WO2007/42469, 2007, A2. Location in patent: Page/Page column 15; 16
  • 3
  • [ 82911-69-1 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
  • 4
  • [ 195071-49-9 ]
  • [ 28920-43-6 ]
  • [ 437655-95-3 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 7, p. 2170 - 2180
  • 5
  • [ 112-60-7 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
  • 6
  • [ 77544-60-6 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
  • 7
  • [ 86770-74-3 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
  • 8
  • [ 86770-67-4 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
  • 9
  • [ 106984-09-2 ]
  • [ 437655-95-3 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
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