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[ CAS No. 73365-02-3 ] {[proInfo.proName]}

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Chemical Structure| 73365-02-3
Chemical Structure| 73365-02-3
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Product Details of [ 73365-02-3 ]

CAS No. :73365-02-3 MDL No. :MFCD01321389
Formula : C10H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YDBPZCVWPFMBDH-MRVPVSSYSA-N
M.W : 199.25 Pubchem ID :7009153
Synonyms :

Calculated chemistry of [ 73365-02-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.79
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 1.16
Log Po/w (WLOGP) : 1.2
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 1.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.54
Solubility : 5.72 mg/ml ; 0.0287 mol/l
Class : Very soluble
Log S (Ali) : -1.73
Solubility : 3.68 mg/ml ; 0.0185 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.95
Solubility : 22.5 mg/ml ; 0.113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 73365-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73365-02-3 ]

* 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 [ 73365-02-3 ]
  • Downstream synthetic route of [ 73365-02-3 ]

[ 73365-02-3 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 59378-81-3 ]
  • [ 73365-02-3 ]
YieldReaction ConditionsOperation in experiment
89% With Dess-Martin periodane In dichloromethane for 1.08333 h; Inert atmosphere 1 49A. tert-Butyl (2R)-2-formylyrrolidine-1 -carboxylateDess-Martin periodinane (15.9 g, 37.4 mmol) was added in portions over 5 minutes toa stirred solution of tert-butyl (2R)-2-(hydroxymethyl)pyrrolidine- 1 -carboxylate (5.0 g,24.9 mmol) in DCM (75 mL) under a nitrogen atmosphere. The resulting suspensionwas stirred for one hour then filtered through a pad of celite washing with DCM (100 mL). The filtrate was evaporated under reduced pressure to leave a residue which was purified by column chromatography on neutral silica gel using 12percent EtOAc/hexanes as the eluent to give the title compound (4.4 g, 89percent).
73%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at 0℃; for 1 h;
DMSO (0.698 g, 8.94 mmcl) was added dropwise to a solution of oxalyl chloride (0.566 g, 2.93mmol) in anhydrous DCM (12 mL) at -78C under nitrogen. The reaction mixture was stirred at - 78CC under nitrogen for 15 mm then a solution of (2R)-(+)-1-Boc-2-pyrrolidmnemethanol (0.600 g, 2.98 mmol) in anhydrous DCM (4 mL) was added dropwise. The reaction mixture was stirredat -7&C under nitrogen for 15 mm then Et3N (1.06 g, 11 .92 mmcl) was added and the reaction mixture was stirred at DC under nitrogen for 1 h. The reaction mixture was quenched with sat. NaHCO3 (aq) (20 mL) and extracted with DCM (2 x 20 mL), the organic layers were combined and dried by passing through a Biotage Phase Separator Cartridge and the solvents were removed in vacuo. The residue was purified by column chromatography (normal phase, [Biotage SNAP cartridge KP-sil log 4O-63im, 60A, l2mL per mm, gradient 0percent 104percent MeOH I DCM]) to give tert-butyl(2R)-2-formylpyrrolidine-1-carboxylate (0.435 g, 73percent).
95 g With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In dichloromethane at -10 - -5℃; Weigh 100g BOC-D-prolinol into a 2L four-neck reaction flask, add 1.5L of dichloromethane, stir at room temperature After dissolution, add 15.5g of sodium bromide, 2.5g of TEMPO, and cool down to -10 °C.Start to add a sodium hypochlorite solution with a pH of 8 to 9 and maintain the temperature at -5 to -10 °C. TLC tracking (developing agent ethyl acetate: petroleum ether = 1:1), after the reaction of the raw materials was completed, stop adding sodium hypochlorite solution (about 500 ml), stratify at rest, leave the organic layer, and use 1percent sulfuric acid solution respectively.800ml, 5percent sodium thiosulfate solution 800ml and saturated saline 800ml each wash once,The organic layer was dried over anhydrous magnesium sulfate. Filtration and evaporation to give BOC-D-prolinal 95 g.
Reference: [1] Patent: WO2015/120390, 2015, A1, . Location in patent: Page/Page column 97; 178
[2] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[3] Patent: WO2015/118342, 2015, A1, . Location in patent: Page/Page column 94; 95
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 12, p. 3190 - 3198
[5] Tetrahedron Letters, 1990, vol. 31, # 28, p. 3957 - 3960
[6] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1550 - 1557
[7] Journal of Medicinal Chemistry, 1994, vol. 37, # 4, p. 439 - 445
[8] European Journal of Organic Chemistry, 1998, # 6, p. 945 - 959
[9] Organic Letters, 2009, vol. 11, # 12, p. 2491 - 2494
[10] Patent: EP1553074, 2005, A1, . Location in patent: Page/Page column 49-50
[11] Patent: US2010/160352, 2010, A1, . Location in patent: Page/Page column 16
[12] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2720 - 2727
[13] Patent: US2011/263561, 2011, A1, . Location in patent: Page/Page column 20-21
[14] Nature, 2014, vol. 509, # 7500, p. 318 - 324
[15] RSC Advances, 2016, vol. 6, # 31, p. 25713 - 25723
[16] Patent: CN108314639, 2018, A, . Location in patent: Paragraph 0069; 0070; 0071
  • 2
  • [ 852324-75-5 ]
  • [ 73365-02-3 ]
YieldReaction ConditionsOperation in experiment
93.2% With triethylsilane In acetone at 0 - 20℃; for 0.5 h; Step B: (2R) -N-Boc-Prolinecarboxyaldehyde To a solution of (2R)-N-Boc-Proline thioester, prepared in Step A, (15.0 g, 6.5 mmol) in acetone was added triethylsilane (5.39 g, 46.3 mmol) and Pd/C (100 mg) at 0°C. When the bubbling was not generated any more, the reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc/Hex = 1/2) to give the title compound (1.43 g, 93.2percent). MS [M+H] = 200 (M+1)
Reference: [1] Patent: WO2005/47253, 2005, A1, . Location in patent: Page/Page column 46
  • 3
  • [ 37784-17-1 ]
  • [ 73365-02-3 ]
YieldReaction ConditionsOperation in experiment
11.1 g
Stage #1: With oxalyl dichloride; triethylamine In dichloromethane; dimethyl sulfoxide at -78℃; for 1.15 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
To a solution of oxalyl chloride (6.39 mL, 75 mmol) in DCM (200 mL) at -78 00 under nitrogen, was added DMSO (10.66 mL, 150 mmol) dropwise, the reaction mixture was stirred at -78 00 for 15 mins. (Teit-butoxycarbonyl)-D-proline (10.0 g, 46.4 mmol) in DCM (50 mL) was added dropwise to the reaction mixture at -78 00 over 1 h and thenthe reaction mixture was stirred at -78 00 for 15 mins. Et3N (28 mL, 200 mmol) was added dropwise to the reaction mixture at -78 00 the reaction mixture was warmed to 0 00 and stirred for 1 h under nitrogen. The reaction mixture was quenched with saturated NaHCO3 (aq) (200 mL), combined aqueous layers washed with DCM (100 mL), the organic layers were combined, dried (Na2SO4) and solvents were removed invacuo to give crude teit-butyl (2R)-2-formylpyrrolidine-1-carboxylate (11.1 g, 100percent) asa colourless oil. Used directly without further purification
Reference: [1] Organic Letters, 2006, vol. 8, # 23, p. 5357 - 5360
[2] European Journal of Medicinal Chemistry, 2000, vol. 35, # 11, p. 979 - 988
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1550 - 1557
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 12, p. 3190 - 3198
[5] Tetrahedron Letters, 1990, vol. 31, # 28, p. 3957 - 3960
[6] Patent: US2011/263561, 2011, A1,
[7] Nature, 2014, vol. 509, # 7500, p. 318 - 324
[8] RSC Advances, 2016, vol. 6, # 31, p. 25713 - 25723
[9] Patent: WO2017/21728, 2017, A1, . Location in patent: Page/Page column 53
  • 4
  • [ 201230-82-2 ]
  • [ 73286-71-2 ]
  • [ 69610-41-9 ]
  • [ 73365-02-3 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2145 - 2151
  • 5
  • [ 79-37-8 ]
  • [ 59378-81-3 ]
  • [ 73365-02-3 ]
Reference: [1] Patent: US5620959, 1997, A,
  • 6
  • [ 288086-98-6 ]
  • [ 73365-02-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2000, vol. 35, # 11, p. 979 - 988
[2] Organic Letters, 2006, vol. 8, # 23, p. 5357 - 5360
  • 7
  • [ 549531-94-4 ]
  • [ 73365-02-3 ]
Reference: [1] Synlett, 2011, # 14, p. 2048 - 2052
  • 8
  • [ 201230-82-2 ]
  • [ 73286-71-2 ]
  • [ 73365-02-3 ]
  • [ 191347-94-1 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 15, p. 4357 - 4362
[2] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1149 - 1152
  • 9
  • [ 73323-65-6 ]
  • [ 73365-02-3 ]
Reference: [1] Chemistry Letters, 1987, p. 2085 - 2088
  • 10
  • [ 24424-99-5 ]
  • [ 73365-02-3 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[2] Patent: US2011/263561, 2011, A1,
[3] Nature, 2014, vol. 509, # 7500, p. 318 - 324
  • 11
  • [ 201230-82-2 ]
  • [ 73286-71-2 ]
  • [ 69610-41-9 ]
  • [ 73365-02-3 ]
  • [ 191347-94-1 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1149 - 1152
  • 12
  • [ 6216-63-3 ]
  • [ 59378-81-3 ]
  • [ 73365-02-3 ]
Reference: [1] Patent: US6130239, 2000, A,
  • 13
  • [ 68832-13-3 ]
  • [ 73365-02-3 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
  • 14
  • [ 344-25-2 ]
  • [ 73365-02-3 ]
Reference: [1] Patent: US2011/263561, 2011, A1,
[2] Nature, 2014, vol. 509, # 7500, p. 318 - 324
  • 15
  • [ 73365-02-3 ]
  • [ 73323-65-6 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2145 - 2151
  • 16
  • [ 73365-02-3 ]
  • [ 37784-17-1 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2145 - 2151
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