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Chemical Structure| 79722-21-7
Chemical Structure| 79722-21-7
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Product Details of [ 79722-21-7 ]

CAS No. :79722-21-7 MDL No. :MFCD00191873
Formula : C12H17NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MZNBNPWFHGWAGH-UHFFFAOYSA-N
M.W : 223.27 Pubchem ID :736159
Synonyms :

Calculated chemistry of [ 79722-21-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.04
TPSA : 47.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 1.59
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.486 mg/ml ; 0.00218 mol/l
Class : Soluble
Log S (Ali) : -3.11
Solubility : 0.172 mg/ml ; 0.000771 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0704 mg/ml ; 0.000316 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.48

Safety of [ 79722-21-7 ]

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 [ 79722-21-7 ]

* 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 [ 79722-21-7 ]
  • Downstream synthetic route of [ 79722-21-7 ]

[ 79722-21-7 ] Synthesis Path-Upstream   1~9

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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1620 - 1625
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YieldReaction ConditionsOperation in experiment
69%
Stage #1: With sodium carbonate In dichloromethane for 1 h;
Stage #2: at 0 - 25℃; for 17 h;
Intermediate 153: tert-butyl benzyloxycarbamate To a solution of O-benzylhydroxylamine hydrochloride (225 g, 1.44 mol) in dichloromethane (300 mL) was added a solution of sodium bicarbonate (261 g, 3.11 mol, 300ml). After 1 hour the di-tert-butyl dicarbonate (375 g, 1.72 mol) was added at 0 °C. The resulting solution was stirred for 60 min at 0 °C in a water/ice bath and then the reaction was stirred for 16 h at room temperature. The reaction was then quenched by the addition of 300 mL of aqueous sodium bicarbonate. The aqueous phase was extracted with 3 x 500 mL of dichloromethane and the organic layers were combined and dried over anhydrous sodium sulfate and concentrated under vacuum. Flash chromatograph on silica gel (PE: EA=10: 1) afforded 220 g (69percent) of the title compound as a yellow oil. 1H MR (300MHz. COCh) δ: 1.43 (9H, s), 4.85 (2H, s), 7.19-7.21 (1H, brs), 7.30-7.40 (5H, m).
50% With dmap; triethylamine In dichloromethane at 20℃; O-Benzyl-hydroxylamine hydrochloride (300 mg, 1.89 mmol) was dissolved in DCM (5 mL).
Triethylamine (1.05 mL, 7.56 mmol), DMAP (catalytic amount) and di-tert-butyldicarbonate (617 mg, 2.83 mmol) were added and the mixture was stirred at room temperature overnight.
Water and DCM were then added.
The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure.
The crude material was purified by preparative TLC on silica gel (DCM/MeOH 99/1) to give compound (116a) (210 mg, 0.94 mmol, 50percent).
91% With triethanolamine In tetrahydrofuran; water; ethyl acetate Nα -tert-Butyloxycarbonyl-O-benzylhydroxylamine (28)
O-Benzyl hydroxylamine hydrochloride (15.9 g, 100 mmol) was suspended in THF (150 ml) and water (50 ml) mixture.
To this stirred mixture was added TEA (15.15 g, 150 mmol) followed by di-tert-butyldicarbonate (23.98 g, 110 mmol).
The reaction mixture was stirred at room temperature for 12 h and evaporated to dryness.
The residue was partitioned between EtOAc (250 ml) and water (200 ml), and extracted in EtOAc.
The EtOAc extract was washed with potassium hydrogen sulfate (100 ml) and brine (100 ml), dried and evaporated to dryness to give 15 g (91percent) of clear oil.
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9148 - 9159
[2] Archiv der Pharmazie, 2016, vol. 349, # 5, p. 373 - 382
[3] Journal of Organic Chemistry, 1983, vol. 48, p. 24
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 24, p. 8549 - 8555
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8847 - 8858
[6] Dalton Transactions, 2015, vol. 44, # 48, p. 20850 - 20858
[7] Patent: WO2013/150296, 2013, A1, . Location in patent: Page/Page column 150; 151
[8] Patent: EP2913330, 2015, A1, . Location in patent: Paragraph 0409
[9] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3183 - 3203
[10] Patent: US6310095, 2001, B1,
[11] Patent: US5969135, 1999, A,
[12] Patent: WO2004/18466, 2004, A2, . Location in patent: Page 10; 7
[13] Organic and Biomolecular Chemistry, 2012, vol. 10, # 17, p. 3519 - 3530
[14] Patent: WO2016/27262, 2016, A1, . Location in patent: Page/Page column 63
  • 3
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YieldReaction ConditionsOperation in experiment
99% at 20℃; for 20 h; ieri-butyl benzyloxycarbamate (150): /V-hydroxybenzyl-amine (1 equivalent, 1 .62 g) was dissolved in 30 ml of THF. Boc20 (1 equivalent, 2.87 g) was added and the reaction mixture is stirred for 20 h at room temperature. The reaction mixture is concentrated and 50 ml of AcOEt are added. The organic phase are washed with 10percent citric acid and brine then dried over Na2S04, filtered and concentrated to afford 150 as an oil (2.92 g, 99percent). H NMR (CDCI3): δ 1 .42 (s, 9H), 4.73 (s, 2H), 7.37 (m, 5H), 10.03 (s, 1 H).
100% With sodium hydroxide In tetrahydrofuran; water EXAMPLE 4
t-Butyl-N-benzyloxycarbamate
To a stirred solution of O-benzylhydroxylamine (16.0 g; 0.13 mol) and di-t-butyldicarbonate (28.4 g; 0.13 mol) in a mixture of water (150 ml) and tetrahydrofuran (150 ml) 2N NaOH solution was added dropwise to adjust the pH to 8-9 and this pH was maintained for an additional 2 hours by occasional addition of 2N NaOH.
After extraction with ethylacetate the combined organic layers were washed with brine, dried (MgSO4) and evaporated in vacuo to leave an oil which was used in the next example without any further purification; yield 29 g (100percent).
Reference: [1] Patent: WO2011/76784, 2011, A2, . Location in patent: Page/Page column 96-97
[2] ChemMedChem, 2017, vol. 12, # 18, p. 1555 - 1571
[3] Journal of Organic Chemistry, 1981, vol. 46, # 26, p. 5438 - 5441
[4] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 13, p. 1753 - 1755
[5] Patent: US5250691, 1993, A,
[6] Patent: US5290929, 1994, A,
[7] Journal of the American Chemical Society, 2008, vol. 130, # 37, p. 12282 - 12284
[8] Tetrahedron Letters, 2009, vol. 50, # 26, p. 3446 - 3449
[9] Synthesis (Germany), 2015, vol. 47, # 2, p. 175 - 180
[10] Journal of Inorganic Biochemistry, 2015, vol. 151, p. 164 - 175
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Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 32, p. 10458 - 10459
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Reference: [1] Patent: US5066658, 1991, A,
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Reference: [1] Tetrahedron Letters, 1989, vol. 30, p. 31 - 34
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  • [ 219547-77-0 ]
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Reference: [1] Chemical Communications, 2000, # 11, p. 975 - 976
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Reference: [1] Synthesis (Germany), 2015, vol. 47, # 2, p. 175 - 180
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Reference: [1] Synthesis (Germany), 2015, vol. 47, # 2, p. 175 - 180
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