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[ CAS No. 26690-80-2 ] {[proInfo.proName]}

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Chemical Structure| 26690-80-2
Chemical Structure| 26690-80-2
Structure of 26690-80-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 26690-80-2 ]

CAS No. :26690-80-2 MDL No. :MFCD00056657
Formula : C7H15NO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :GPTXCAZYUMDUMN-UHFFFAOYSA-N
M.W :161.19 Pubchem ID :2733206
Synonyms :
Boc-NH-PEG1-OH

Calculated chemistry of [ 26690-80-2 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.44
TPSA : 58.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 0.24
Log Po/w (WLOGP) : 0.5
Log Po/w (MLOGP) : 0.3
Log Po/w (SILICOS-IT) : -0.03
Consensus Log Po/w : 0.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.66
Solubility : 35.2 mg/ml ; 0.218 mol/l
Class : Very soluble
Log S (Ali) : -1.03
Solubility : 15.0 mg/ml ; 0.0933 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.05
Solubility : 14.2 mg/ml ; 0.0881 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 26690-80-2 ]

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

Application In Synthesis of [ 26690-80-2 ]

* 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 [ 26690-80-2 ]
  • Downstream synthetic route of [ 26690-80-2 ]

[ 26690-80-2 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
96% With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 1 h; 32) Preparation of bromide from alcohol,; To a stirred solution of (1 mmol., 1 equiv.) appropriate alcohol in 6 ml of anhydrous dichloromethane at 0°C were added successively 365 mg (1.1 mmol., 1.1 equiv.) of carbon tetrabromide and 287 mg (1.1 mmol., 1.1 equiv.) of triphenylphosphine. The reaction was pursued at 0°C for I h. The mixture was evaporated and purified on silica gel as below or was used whithout purification for "one-pot" alkylation procedure.Preparation of(2-Bromo-ethyl)-carbamic acid tert-butyl ester (Intermediate): [Show Image] Flash chromatography on silica gel (methylene chloride/methyl alcohol 98/2) Colorless oil (96percent) 1H NMR (400 MHz, CDCl3) δ 4.96 (sb, 1H, NH), 3.53 (m, 2H, NCH2CH2Br), 3.45 (m, 2H, NCH2CH2Br), 1.45 (s, 9H, tBu) LC/MS (ES+) m/z 224.1 (M+H)+
1.39 g With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 25℃; Inert atmosphere Under argon atmosphere, to a solution of 1.00 g (6.20 mmol) of N-Boc-ethanolamine in 20 mL of DCM was added 2.47 g (7.44 mmol) of CBr4 and 1.95 g (7.44 mmol) of PPh3 at 0°C. The resulting mixture was stirred at rt for 1 h. TLC showed the reaction was complete. The solution was removed and the residue was purified by silica gel chromatography column (PE/EA = 5/1, Rf= 0.7) to give 1.39 g of product as acolorless oil.‘H NMR (400 MHz, CDC13) ppm: 3.53-3.45 (m, 4H), 1.44 (s, 9H).
Reference: [1] Patent: EP1997805, 2008, A1, . Location in patent: Page/Page column 89-90
[2] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2226 - 2232
[3] Patent: WO2016/128465, 2016, A1, . Location in patent: Page/Page column 90
  • 2
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YieldReaction ConditionsOperation in experiment
40% With triphenylphosphine In dichloromethanol EXAMPLE 16
(2-Bromo-ethyl)-carbamic acid tert-butyl ester
A solution of triphenylphosphine (38.1 g, 145 mol) in 3:2 ether-methylene chloride (300 mL) was treated portionwise with carbon tetrabromide (48.2 g, 145 mmol).
After 10 min, (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (15.6 g, 96.8 mmol) was added via pipet and the mixture stirred under nitrogen.
After 24 h, the reaction mixture was vacuum filtered, washed with ether and the filtrate concentrated to give an orange oil (39.6 g).
Flash chromatography (600 g silica; CH2Cl2, then 1percent, 2percent and 4percent MeOH-CH2Cl2) gave the title compound (5.1 g, 40percent yield based on recovered (2-hydroxy-ethyl)-carbamic acid tert-butyl ester, 6.3 g) as a clear, colorless oil.
1H NMR (DMSO-d6, 300 MHz): δ1.37 (s, 9H, CH3), 3.28 (m, 2H, NCH2), 3.41 (t, J=6.5 Hz, 2H, CH2Br), 7.09 (broad m, 1H, NH).
Reference: [1] Patent: US6429214, 2002, B1,
  • 3
  • [ 558-13-4 ]
  • [ 26690-80-2 ]
  • [ 39684-80-5 ]
Reference: [1] Patent: US6774130, 2004, B2,
[2] Patent: US2002/28823, 2002, A1,
  • 4
  • [ 558-13-4 ]
  • [ 26690-80-2 ]
  • [ 603-35-0 ]
  • [ 39684-80-5 ]
Reference: [1] Patent: US6492366, 2002, B1,
  • 5
  • [ 24424-99-5 ]
  • [ 26690-80-2 ]
  • [ 1972-28-7 ]
  • [ 13036-02-7 ]
Reference: [1] Patent: EP1227084, 2002, A1,
  • 6
  • [ 26690-80-2 ]
  • [ 89711-08-0 ]
YieldReaction ConditionsOperation in experiment
69% With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; Inert atmosphere A round-bottom flask was charged with 48 (0.80 g, 10.0 mmol)and IBX36 (2.80 g, 10.0 mmol) under argon atmosphere. DMSO(25 mL) was added to the mixture and then stirring was continued overnight at rt. The reaction mixture was quenched with water(200 mL) and filtered under reduced pressure. The filtrate was extracted with ethyl acetate. The organic layer was dried (Na2SO4)and concentrated under reduced pressure. Purification of the crude residue by SiO2 column chromatography (CHCl3:EtOAc = 7:3) gave49 (69percent; lit. 55percent37) as an oil; 1H NMR (500 MHz, CDCl3): d 9.65 (2H,br s, HCO), 5.16 (1H, br, NH), 4.06 (2H, s, CH2), 1.45 (9H, s, C(CH3)3).
66% With sulfur trioxide pyridine complex In dimethyl sulfoxide at 20℃; Ice cooling Reference Example 1 tert-Butyl (2-oxoethyl) carbamateTo a mixed solution of tert-butyl (2- hydroxyethyl) carbamate (10.0 g) in dimethyl sulfoxide (50 mL) and triethylamine (12.3 g) was added sulfur trioxide pyridine complex (15.0 g) under ice-cooling, and the mixture was stirred for 1 hr. The reaction mixture was further stirred at room temperature for 3 hr, 1 mol/L hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layers were washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent :hexane-ethyl acetate=17 : 3-->13 : 7) to give the title compound as a pale-yellow oil (yield 6.50 g, 66percent). 1H-NMR (CDCl3) δ:l.46 ( 9H, s) , 4.08 (2H, d, J=4.5Hz) , 5.19 (lH,brs) , 9.66(lH,s) .
14% With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 1 h; Oxalyl chloride (1.3 mL, 15 mmol) was added to a reaction chamber containing methylene chloride (120 mL) at -78° C. and a solution of dimethyl sulfoxide (2.45 mL, 30 mmol) dissolved in methylene chloride (20 mL) was added. The resulting solution was stirred for 10 minutes at -78° C. A solution of N-Boc-ethanolamine (2 g, 12.4 mmol) dissolved in methylene chloride (20 mL) was slowly added and then triethylamine (8.64 ml, 62 mmol) was added. The resulting solution was stirred for 30 minutes at -78° C. and additional 30 minutes at room temperature, washed with water (100 mL) and saline (100 mL). The organic layer was dehydrated with anhydrous sodium sulfate, concentrated under reduced pressure, and applied to column chromatography (n-hex:EA=3:11:1) to yield Compound I (270 mg (14percent)).1H NMR (600 MHz, DMSO-d6) δ=7.83 (s, 1H), 7.49 (s, 1H), 6.88 (d, J=5.4 Hz, 1H), 6.36 (br, 2H), 4.81 (br, 1H), 3.13 (m, 4H), 1.39 (s, 9H)
14% With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 1.16667 h; Oxalyl chloride (1.3 mL, 15 mmol) was added to a reaction chamber containing methylene chloride (120 mL) at -78°C and a solution of dimethyl sulfoxide (2.45 mL, 30 mmol) dissolved in methylene chloride (20 mL) was added. The resulting solution was stirred for 10 minutes at -78°C. A solution of N-Boc-ethanolamine (2g, 12.4 mmol) dissolved in methylene chloride (20 mL) was slowly added and then triethylamine (8.64 ml, 62 mmol) was added. The resulting solution was stirred for 30 minutes at -78°C and additional 30 minutes at room temperature, washed with water (100 mL) and saline (100 mL). The organic layer was dehydrated with anhydrous sodium sulfate, concentrated under reduced pressure, and applied to column chromatography (n-hex : EA = 3 :1∼1:1) to yield Compound I (270 mg (14percent)). 1H NMR (600MHz, DMSO-d6) δ= 7.83(s, 1H), 7.49(s, 1H), 6.88(d, J = 5.4Hz, 1H), 6.36(br, 2H), 4.81(br, 1H), 3.13(m, 4H), 1.39(s, 9H)
80% With triethylamine In dichloromethane; dimethyl sulfoxide Step B:
2-(t-Butoxycarbonylamino)acetaldehyde
To a solution of 700 mg (4.34 mmol) of 2-(t-butoxycarbonylamino)ethanol in 35 mL of dry methylene chloride was added 4.0 mL of dimethylsulfoxide and 4.8 mL (35 mmol) of triethylamine, followed by 2.8 g (17 mmol) of pyridine sulfur trioxide complex in three portions over 5 minutes.
The reaction was stirred at room temperature for 3 hours then diluted with 500 mL of ether.
The mixture was transferred to a separatory funnel and washed with 1N HCl (2*50 mL), saturated aqueous sodium bicarbonate (100 mL), and brine (100 mL).
The organic layer was dried over magnesium sulfate, filtered, and the solvent removed under vacuum to afford 550 mg (80percent) of product which was used without further purification. 1 H NMR (200 MHz,CDCl3): 1.40 (s,9H), 4.05 (d,7 Hz,2H), 5.17 (s,1H), 9.62 (s,1H).
80% With triethylamine In dichloromethane; dimethyl sulfoxide Step C:
N-(t-Butoxycarbonyl)glycinal
To a solution of 700 mg (4.34 mmol) of 2-(t-butoxycarbonylamino)ethanol in 35 mL of dry methylene chloride was added 4.8 mL (35 mmol) of triethylamine and 4.0 mL of dry dimethylsulfoxide.
To the resulting solution was added in portions 2.8 g (17 mmol) of pyridine-sulfur trioxide complex.
The resulting brown solution was s stirred at room temperature for 3 hours.
The mixture was diluted with 500 mL of ether and transferred to a separatory funnel.
The mixture was washed with 1N aqueous hydrochloric acid (2*50 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL).
The organic layer was removed, dried over magnesium sulfate, filtered and the solvent removed under vacuum to afford 550 mg (80percent) of the product as an oil. 1 H NMR (200 MHz, CDCl3): δ1.42 (s, 9H), 4.04 (d, 4 Hz, 2H), 5.18 (s, 1H), 9.62 (s, 1H).
2 g With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 16 h; Step 2: Preparation of tert-butyl (2-oxoeth l)carbamate To a solution of tert-butyl (2-hydroxyethyl)carbamate (4 g, 24.81 mmol) in DCM (200 mL) was added Dess-Martin reagent (12.62 g, 29.77 mmol) at 0 °C. The reaction was stirred at ambient temperature for 16 h. Saturated aqueous Na2C03 (80 mL) and Na2S203 (80 mL) were added to the reaction and stirred for lh. The resulting biphasic mixture was transfered to a separatory funnel. The layers were separated and the aqueous phase was extracted with DCM (3 x 200 mL). The combined organics were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with an isocratic elution of EtOAc (10percent) and hexanes (90 percent) to provide tert-butyl (2- oxoethyl)carbamate (2 g, 12.56 mmol) as a colorless oil. LCMS [M+H]+ = 160.1.

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Reference: [1] Patent: US2005/165089, 2005, A1, . Location in patent: Page/Page column 35
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Reference: [1] Synthesis, 1990, p. 366 - 368
  • 9
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  • [ 97308-23-1 ]
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  • 11
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  • [ 188528-95-2 ]
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  • 12
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  • [ 845267-78-9 ]
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  • 13
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  • [ 159184-15-3 ]
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  • 14
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  • [ 159184-14-2 ]
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  • [ 159184-14-2 ]
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  • 16
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  • [ 1170390-54-1 ]
Reference: [1] Patent: WO2011/29046, 2011, A1,
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