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[ CAS No. 220199-85-9 ] {[proInfo.proName]}

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Chemical Structure| 220199-85-9
Chemical Structure| 220199-85-9
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Product Details of [ 220199-85-9 ]

CAS No. :220199-85-9 MDL No. :MFCD11111782
Formula : C9H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JDDPITNKUXPLSB-UHFFFAOYSA-N
M.W : 187.24 Pubchem ID :11435389
Synonyms :

Calculated chemistry of [ 220199-85-9 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.87
TPSA : 38.77 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) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.27
Solubility : 10.1 mg/ml ; 0.0538 mol/l
Class : Very soluble
Log S (Ali) : -1.13
Solubility : 13.8 mg/ml ; 0.0736 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.97
Solubility : 20.2 mg/ml ; 0.108 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.38

Safety of [ 220199-85-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 220199-85-9 ]

* 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 [ 220199-85-9 ]
  • Downstream synthetic route of [ 220199-85-9 ]

[ 220199-85-9 ] Synthesis Path-Upstream   1~9

  • 1
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YieldReaction ConditionsOperation in experiment
100% With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.0166667 h; General procedure: Amine (1 mmol) was added to a magnetically stirred solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (1.2 mmol) in EtOH (1 mL), at 35-40°C and stirred for appropriate time (Table 1). After completion of the reaction (followed by TLC or GC), EtOH was evaporated under vacuum and the residue either was washed with water to remove the catalyst or was dissolved in CH2Cl2 (or EtOAc) and filtered off to separate out the catalyst. Evaporation of the organic solvent (if used in work up) gives almost a pure product. In the cases of using an excess (Boc)2O the product was washed with petroleum ether or hexane to recover the residual (Boc)2O. If necessary, the product was further purified either by crystallization (hexane and dichloromethane, or diethyl ether and petroleum ether) or silica gel column chromatography using EtOAc-hexane (1: 6) as eluent.
99% at 20℃; for 0.166667 h; Ionic liquid To the ionic liquid [TPA][Pro] (1 mL) was added amine (1-14; Table-1) (1 mmol) and di-tert-butyl dicarbonate (1.2 mmol). The reaction was stirred at room temperature for an appropriate time (Table-1). After completion of the reaction as monitored by TLC, water was added to the reaction mixture and the product was extracted into ethyl acetate (3 × 20 mL). The combined organic layer was washed with brine solution and concentrated under reduced pressure to give crude product, which was purified over silica gel column to afford corresponding N-tert-butylcarbamate. The ionic liquid [TPA][Pro] in aqueous solution was recovered by removing water under reduced pressure and dried. The recovered ionic liquid was reused for five times without loss of its activity. Finally, all the compounds confirmed by their m.p.’s, IR, 1H NMR, 13C NMR, mass spectral data and elemental analysis wherever needed.
96% With Amberlyst® A21 In neat (no solvent) at 20℃; for 0.0333333 h; Green chemistry General procedure: Amberlyst® A21 (20 wt percent) was added to a mixture of amine (1 mmole) and (Boc)2O (1 mmole) and the mixture was stirred for the appropriate reaction time as specified in (Table 1). The progress of reaction was monitored by Thin layer chromatography (10-20percent ethyl acetate: hexane) on TLC plates (Merck) precoated with silica. After completion of reaction, the reaction mass was diluted with methanol, filtered off the catalyst which was washed for several times and then dried at 800 °C under reduced pressure for 1 hour and subjected to further recycle study (Table 4). It showed no much more decrease in the product yield indicating high activity of the catalyst. The filtrate was concentrated on rotavacc and the product was purified by column chromatography to afford pure products.
96% With phenylsulfonic acid supported on mesoporous silica SBA-15 In neat (no solvent) at 20℃; for 0.05 h; Green chemistry General procedure: An amine (1 mmol) was added to a magnetically stirred mixture of SBA-15-Ph-SO3H (1 mol percent, 4 mg) and (Boc)2O (1.1 mmol) at room temperature. The progressof the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was diluted with EtOH (5 mL)and centrifuged. Then the clear liquid was separated, and the residue containing the catalyst was kept for recovery. EtOH was distilled off under vacuum to yield the highly pure N-Boc derivative.
95% at 100℃; for 0.0333333 h; Microwave irradiation; Green chemistry General procedure: Amine (1 mmol) and di-tert-butyl dicarbonate [(Boc)2O] (1.1 mmol) were placed in a microwave reaction vial. The LG microwave oven MG 555f was programmed to 300 W at 100 °C. The reaction was monitored using TLC. After the reaction, ice water was added to the reaction mixture which resulted in the precipitation of the product. The solid product was merely filtered off and washed with excess cold water. The product was pure enough for all practical purposes. For characterization purpose, it was further purified by column chromatography (Neutral Alumina as adsorbent, solvent system: Hexane: Ethyl acetate (7.5:2.5)).#10;
94% at 20℃; for 0.05 h; Green chemistry General procedure: To (Boc)2O (1.0 mmol), was added an amine (1.0 mmol)and the mixture was stirred at room temperature for the time indicated in Table 1. The progress of the reaction was monitored by TLC. In most cases, the BOC protected product was found to be sufficiently pure and did not require any further purification. In some cases the product was purified by silica gel column chromatography (1:2; EtOAc/ Petrolium ether).All products were characterized by IR, 1H NMR and their physical properties.
94% With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.0833333 h; Green chemistry General procedure: Fe(OTf)3 (1 molpercent) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N‑Boc derivatives

Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 46, p. 8039 - 8042
[2] Synthesis, 2006, # 16, p. 2784 - 2788
[3] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2527 - 2532
[4] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264
[5] Monatshefte fur Chemie, 2011, vol. 142, # 10, p. 1035 - 1043
[6] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322
[7] Tetrahedron Letters, 2008, vol. 49, # 21, p. 3527 - 3529
[8] Synthesis, 2008, # 19, p. 3126 - 3130
[9] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6244 - 6246
[10] Asian Journal of Chemistry, 2017, vol. 29, # 6, p. 1313 - 1316
[11] Organic Letters, 2006, vol. 8, # 15, p. 3259 - 3262
[12] Comptes Rendus Chimie, 2010, vol. 13, # 5, p. 544 - 547
[13] Synthetic Communications, 2012, vol. 42, # 1, p. 25 - 32
[14] Letters in Organic Chemistry, 2011, vol. 8, # 1, p. 38 - 42
[15] Letters in Organic Chemistry, 2012, vol. 9, # 3, p. 165 - 168
[16] RSC Advances, 2016, vol. 6, # 82, p. 78576 - 78584
[17] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 577 - 580
[18] Tetrahedron Letters, 2010, vol. 51, # 29, p. 3855 - 3858
[19] Tetrahedron Letters, 2006, vol. 47, # 43, p. 7551 - 7556
[20] Journal of the Chilean Chemical Society, 2013, vol. 58, # 1, p. 1619 - 1623
[21] Research on Chemical Intermediates, 2016, vol. 42, # 2, p. 1451 - 1461
[22] New Journal of Chemistry, 2018, vol. 42, # 12, p. 10142 - 10147
[23] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[24] Tetrahedron Letters, 2012, vol. 53, # 43, p. 5803 - 5806
[25] Letters in Organic Chemistry, 2013, vol. 10, # 2, p. 121 - 125
[26] Journal of Chemical Research, 2013, vol. 37, # 12, p. 757 - 760
[27] Tetrahedron Letters, 2010, vol. 51, # 49, p. 6388 - 6391
[28] Synthetic Communications, 2011, vol. 41, # 5, p. 715 - 719
[29] Synlett, 2006, # 7, p. 1110 - 1112
[30] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6963 - 6965
[31] Advanced Synthesis and Catalysis, 2005, vol. 347, # 15, p. 1929 - 1932
[32] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5865 - 5868
[33] Tetrahedron Letters, 2017, vol. 58, # 7, p. 629 - 633
[34] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8051 - 8055
[35] Organic Letters, 2018, vol. 20, # 18, p. 5661 - 5665
  • 2
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  • [ 49761-82-2 ]
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YieldReaction ConditionsOperation in experiment
88% With Imidazole hydrochloride In water at 20℃; for 0.166667 h; General procedure: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 19, p. 2373 - 2376
  • 3
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Reference: [1] RSC Advances, 2014, vol. 4, # 47, p. 24544 - 24550
  • 4
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  • [ 1538-75-6 ]
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2012, vol. 51, # 8, p. 1168 - 1172,5
  • 5
  • [ 110-91-8 ]
  • [ 89985-91-1 ]
  • [ 220199-85-9 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 5, p. 1547 - 1550
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1115 - 1119
  • 6
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Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6368 - 6380
  • 7
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Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 9, p. 2971 - 2975
  • 8
  • [ 24424-99-5 ]
  • [ 25070-77-3 ]
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 32, p. 5741 - 5744
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Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 9, p. 2971 - 2975
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