Home Cart 0 Sign in  

[ CAS No. 91103-47-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 91103-47-8
Chemical Structure| 91103-47-8
Structure of 91103-47-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 91103-47-8 ]

Related Doc. of [ 91103-47-8 ]

Alternatived Products of [ 91103-47-8 ]

Product Details of [ 91103-47-8 ]

CAS No. :91103-47-8 MDL No. :MFCD00191865
Formula : C9H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :GJDICGOCZGRDFM-ZCFIWIBFSA-N
M.W : 203.24 Pubchem ID :637612
Synonyms :

Calculated chemistry of [ 91103-47-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.18
TPSA : 64.63 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) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.67
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.07
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 1.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.22
Solubility : 12.2 mg/ml ; 0.0602 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 3.54 mg/ml ; 0.0174 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.35
Solubility : 9.1 mg/ml ; 0.0448 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.73

Safety of [ 91103-47-8 ]

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 [ 91103-47-8 ]

* 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 [ 91103-47-8 ]
  • Downstream synthetic route of [ 91103-47-8 ]

[ 91103-47-8 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 91103-47-8 ]
  • [ 82353-56-8 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With diisobutylaluminium hydride In toluene at -78℃; for 1 h;
Stage #2: With methanol In toluene at -78℃; for 0.166667 h;
Stage #3: With methanol; water; citric acid In toluene at 0℃; for 1 h;
Example 46(1-Methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester The title compound from Example 45 (3.53 g, 17.4 mmol) was dissolved in toluene (35 mL) at -78° C. and DIBAL-H (26.6 mL, 39.9 mmol) was added dropwise over 1 hour. Methanol (70 mL) was added to the reaction over 10 min. at -78° C. The reaction was moved to an ice bath and 10percent w/v citric acid in water (250 mL) was added and the reaction was allowed to stir for 1 hour. The reaction was extracted with portions of ethyl acetate and the organic extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (2.57 g, 85percent) as a white semi-solid.1H NMR (300 MHz, CDCl3): δ (ppm) 9.51 (s, 1H), 5.21 (broad s, 1H), 4.24 (broad s, 1H), 1.53 (s, 9H), 1.35 (d, 3H).
82%
Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane at -78℃; for 2 h;
Stage #2: With water In tetrahydrofuran; dichloromethane at -78℃;
Step 1: (R)-tert-butyl 1-oxopropan-2-ylcarbamateTo a cooled solution of (R)-methyl 2-(tert-butoxycarbonylamino)propanoate (40.0 g, 98.0 mmol) in DCM (200 mL) at -78° C. was added diisobutylaluminum hydride (208 mL, 1.0 M in THF) dropwise over 30 min. The reaction mixture was stirred at -78° C. for 1.5 h then quenched with water (50 mL). After warmed to rt, the white precipitate was removed by filtration over Celite. The organic layer was then washed with brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1) to give (R)-tert-butyl 1-oxopropan-2-ylcarbamate (28.0 g, 82percent). 1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 7.33 (d, J=6.0 Hz, 1H), 3.85 (m, 1H), 1.39 (s, 9H), 1.12 (d, J=7.2 Hz, 3H).
65% With diisobutylaluminium hydride In toluene at -78℃; for 2 h; EXAMPLE 49; (R)-5-Chloro-thiophene-2-carboxylic acid (1 - {3-[4-(N,N-dimethyl-carbamimidoyl)-phenyl]- isoxazol-5-yl}-ethyl)-amide; Step l :; [0553] Methyl ester 8 (4.03 g, 19.9 mmol) was diluted with 40 mL of toluene and cooled to -780C. Diisobutylaluminum hydride in toluene (26 mL, 40 mmol) was added slowly to the precooled mixture down the side of the flask. The reaction was stirred at -780C for two hours at which time it was treated slowly with ca. 5 mL of methanol precooled to -780C (vigorous reaction). The mixture was then warmed to it and partitioned with saturated sodium potassium tartrate and ethyl acetate. The layers were separated, the organic phase was extracted with ethyl acetate and the combined organic layers were dried over MgSO4. After filtration and concentration in vacuo the crude material was purified by filtration through a short plug of silica gel eluted with dichloromethane affording the aldehyde 9 as a colorless oil (2.23g, 65percent). 1H NMR (DMSO-J6, 400 MHz): δ 9.38 (s, IH), δ 7.30 (d, IH), δ 3.79 (m, IH), δ 1.31 (s, 9H), 1.06 (d, 3H).
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1886 - 1890
[2] Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 8, p. 629 - 630
[3] Patent: US2007/259860, 2007, A1, . Location in patent: Page/Page column 34-35
[4] Patent: US2011/213003, 2011, A1, . Location in patent: Page/Page column 73
[5] Organic and Biomolecular Chemistry, 2003, vol. 1, # 16, p. 2983 - 2997
[6] Journal of the American Chemical Society, 2016, vol. 138, # 49, p. 15798 - 15800
[7] Liebigs Annalen der Chemie, 1992, # 2, p. 131 - 138
[8] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 10, p. 2702 - 2706
[9] Heterocycles, 1988, vol. 27, # 9, p. 2077 - 2080
[10] Patent: WO2006/2099, 2006, A2, . Location in patent: Page/Page column 94-95
[11] Tetrahedron, 2016, vol. 72, # 30, p. 4518 - 4522
[12] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2299 - 2306
[13] Journal of Medicinal Chemistry, 1989, vol. 32, # 1, p. 165 - 170
[14] Journal of Organic Chemistry, 1998, vol. 63, # 1, p. 92 - 98
[15] Tetrahedron Asymmetry, 2001, vol. 12, # 11, p. 1543 - 1545
[16] Journal of Organic Chemistry, 1987, vol. 52, # 7, p. 1252 - 1255
[17] Tetrahedron, 2009, vol. 65, # 1, p. 357 - 363
[18] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2812 - 2815
[19] Angewandte Chemie - International Edition, 2012, vol. 51, # 21, p. 5239 - 5243
[20] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 1, p. 37 - 41
  • 2
  • [ 24424-99-5 ]
  • [ 14316-06-4 ]
  • [ 91103-47-8 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydrogencarbonate In water at 20℃; To a solution of D-alanine methyl ester hydrochloride (5 g, 35.8 mmol) and sodium hydrogen carbonate (9.0 g, 107 mmol) in water (100 mL) was added di-tert-butyl dicarbonate (11.7 g, 53.7 mmol) and the resulting solution was stirred at RTovernight. The reaction mixture was extracted with DCM (3 x 100 mL) and the combined organics were dried over MgSO4, filtered and concentrated under reduced pressure. Crude NMR revealed large amounts of un-reacted di-tert-butyl dicarbonate, hence the material was taken up in DCM (50 mL) and treated with N,N-dimethyl ethylenediamne (5 mL), and stirred for 30 mins. The solution waswashed with 1M HCI (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to afford 5.35 g (73percent yield) of the title compound as a colourless oi I.1H NMR (500 MHz, Chloroform-d) 6 5.04 (5, 1 H), 4.31 (m, 1 H), 3.73 (5, 3H), 1 .44 (5, 9H), 1.37 (d, J = 7.2 Hz, 3H).
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2299 - 2306
[2] Patent: WO2016/91776, 2016, A1, . Location in patent: Page/Page column 387
[3] Heterocycles, 1988, vol. 27, # 9, p. 2077 - 2080
[4] Journal of Organic Chemistry, 1998, vol. 63, # 1, p. 92 - 98
[5] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 387 - 398
  • 3
  • [ 3744-87-4 ]
  • [ 74-88-4 ]
  • [ 91103-47-8 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25 h;
Stage #2: for 18 h;
Intermediate 57 Boc-D-AlaOMe Boc-D-AlaOH (10.0 g, 52.9 mmol) was dissolved in dry DMF (60 mL), then potassium carbonate (8.0 g, 58.0 mmol) was added, the mixture was stirred at rt for 15 min, and methyl iodide (6.58 mL, 106.0 mmol) was added dropwise. The stirring was maintained for 18h. Then, the mixture was concentrated in vacuo and the residue was dissolved in EtOAc (lOOmL). The organic layer was washed with water, brine, dried over MgSCU, filtered and concentrated. The crude product was purified by flash column chromatography (silica gel, DCM/MeOH 0 to 1percent) to give 10.36 g (51.0 mmol, 96percent yield) of the title compound. *Η NMR (DMSO-d6) δ 7.46 (1H, d), 4.35 (1H, m), 3.66 (3H, s), 1.30 (9H, s), 1.18 (3H, d).
82% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Example 452-tert-Butoxycarbonylamino-propionic acid methyl ester Boc-D-Ala-OH (4.0 g, 21 mmol) and potassium carbonate (11.7 g, 84.6 mmol) was dissolved in dimethylformamide (90 mL) and iodomethane (1.6 mL, 25 mmol) was added to the reaction mixture. The reaction was allowed to stir at room temperature. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with portions of water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound as a colorless oil (3.53 g, 82percent).1H NMR (300 MHz, CDCl3): δ (ppm) 5.14 (broad s, 1 h), 4.33 (broad s, 1H), 3.51 (s, 3H), 1.49 (s, 9H).
Reference: [1] Patent: WO2016/8946, 2016, A1, . Location in patent: Page/Page column 72-73
[2] Patent: US2007/259860, 2007, A1, . Location in patent: Page/Page column 34
[3] Journal of Organic Chemistry, 1987, vol. 52, # 7, p. 1252 - 1255
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 21, p. 5239 - 5243
  • 4
  • [ 24424-99-5 ]
  • [ 204126-98-7 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 7, p. 2371 - 2374
  • 5
  • [ 24424-99-5 ]
  • [ 7625-53-8 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4430 - 4448
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7976 - 7996
[3] Patent: WO2015/95128, 2015, A1, . Location in patent: Paragraph 0209; 0212; 0213
  • 6
  • [ 112392-66-2 ]
  • [ 28875-17-4 ]
  • [ 91103-47-8 ]
YieldReaction ConditionsOperation in experiment
85.91 % ee With water In aq. phosphate buffer; N,N-dimethyl-formamide at 30℃; for 6 h; General procedure: The soil samples were collected from various locations inChina, and then the strains were screened by utilizing N-Boc-2-aminobutyrate as a sole carbon source and selective platewith bromocresol purple indicator. Isolated strains weretransferred to 150 mL fermentation medium and cultivatedat 200 rpm, 30 °C for 48 h. After the cells were harvested, 1 g wet cell were washed and suspended in 5 mL 0.1 M,pH 7.0 potassium phosphate buffer (KPB). Cell suspensionswere mixed with 50 μL substrate solution (N-Boc-2-aminobutyrate:acetone = 1:4,V/V) and kept at 200 rpm, 30 °Cfor 6 h reaction, the enantioselective hydrolysis of the substratewas determined by GC-MS. The screening mediumcontained (per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O,1 g K2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,0.25 g Bromocresolpurple, 20 g agar. Fermentation medium contained(per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O, 1 gK2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,20 g sucrose.
Reference: [1] Catalysis Letters, 2017, vol. 147, # 4, p. 837 - 844
  • 7
  • [ 147751-23-3 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
  • 8
  • [ 112392-66-2 ]
  • [ 15761-38-3 ]
  • [ 91103-47-8 ]
YieldReaction ConditionsOperation in experiment
99.7 % ee With lyophilized cells of Bacillus amyloliquefaciens WZZ002 In aq. phosphate buffer at 35℃; for 10 h; Enzymatic reaction Enantioselective hydrolysis was performed on Boc-dl-Ala-OMe by adding both a substrate with a concentration range of 0.1 to 4.0M and a 500mg lyophilized cell of B. amyloliquefaciens WZZ002 in a 10mL (50mL flask) phosphate buffer solution (0.2M, pH6.0–12.0) at 20°C to 60°C. The solution was stirred at 400rpm. The pH level was controlled through automatic titration using different alkali solutions (2M). The samples were withdrawn at regular intervals and were immediately acidified with HCl (2M) to stop the reaction and to enhance the extractability of Boc-dl-Ala. The sample was extracted using ethyl acetate, whereas the organic phase was isolated and dried using anhydrous Na2SO4 for gas chromatography (GC) analysis. All experiments were conducted in triplicate, unless specified. The time course of enantioselective hydrolysis reaction was performed by adding 2M of Boc-dl-Ala-OMe and 5g of the lyophilized cell of B. amyloliquefaciens WZZ002 in 100mL (250mL flask) phosphate buffer solution (0.2M, pH8.0). The pH of the reaction was controlled through automatic titration using 6M of NH3·H2O to reduce the increasing amount of the neutralizer.
Reference: [1] Catalysis Communications, 2014, vol. 60, p. 134 - 137
  • 9
  • [ 67-56-1 ]
  • [ 139928-91-9 ]
  • [ 91103-47-8 ]
Reference: [1] Chemical Communications, 1997, # 11, p. 1017 - 1018
  • 10
  • [ 24424-99-5 ]
  • [ 91103-47-8 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 52, p. 9691 - 9693
  • 11
  • [ 502162-48-3 ]
  • [ 91103-47-8 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 52, p. 9691 - 9693
  • 12
  • [ 1070-19-5 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
[2] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
[3] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
  • 13
  • [ 147751-16-4 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
[2] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
  • 14
  • [ 145387-82-2 ]
  • [ 91103-47-8 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 10, p. 2900 - 2903
  • 15
  • [ 79069-13-9 ]
  • [ 91103-47-8 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 52, p. 9691 - 9693
  • 16
  • [ 338-69-2 ]
  • [ 91103-47-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1992, # 2, p. 131 - 138
  • 17
  • [ 3744-87-4 ]
  • [ 18107-18-1 ]
  • [ 91103-47-8 ]
Reference: [1] MedChemComm, 2015, vol. 6, # 2, p. 300 - 305
  • 18
  • [ 3744-87-4 ]
  • [ 28875-17-4 ]
  • [ 91103-47-8 ]
Reference: [1] Catalysis Letters, 2017, vol. 147, # 4, p. 837 - 844
  • 19
  • [ 186581-53-3 ]
  • [ 3744-87-4 ]
  • [ 91103-47-8 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 52, p. 9691 - 9693
  • 20
  • [ 91103-47-8 ]
  • [ 100927-10-4 ]
Reference: [1] Patent: US2015/284362, 2015, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 91103-47-8 ]

Amino Acid Derivatives

Chemical Structure| 69942-12-7

[ 69942-12-7 ]

Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate

Similarity: 0.96

Chemical Structure| 2766-43-0

[ 2766-43-0 ]

Boc-Ser-OMe

Similarity: 0.96

Chemical Structure| 95715-85-8

[ 95715-85-8 ]

Boc-D-Ser-OMe

Similarity: 0.96

Chemical Structure| 1146954-88-2

[ 1146954-88-2 ]

(R)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate

Similarity: 0.94

Chemical Structure| 7738-22-9

[ 7738-22-9 ]

Boc-Ser-OtBu

Similarity: 0.94