Home Cart 0 Sign in  

[ CAS No. 1142-20-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1142-20-7
Chemical Structure| 1142-20-7
Structure of 1142-20-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1142-20-7 ]

Related Doc. of [ 1142-20-7 ]

Alternatived Products of [ 1142-20-7 ]

Product Details of [ 1142-20-7 ]

CAS No. :1142-20-7 MDL No. :MFCD00002640
Formula : C11H13NO4 Boiling Point : -
Linear Structure Formula :HO2CCH(NHCOOCH2C6H5)CH3 InChI Key :TYRGLVWXHJRKMT-QMMMGPOBSA-N
M.W : 223.23 Pubchem ID :736104
Synonyms :
(S)-2-(Benzyloxycarbonylamino)propanoic acid;L-Alanine, N-carboxy-, N-benzyl ester (6CI,7CI);N-[(Benzyloxy)carbonyl]-L-alanine
Chemical Name :((Benzyloxy)carbonyl)-L-alanine

Calculated chemistry of [ 1142-20-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 56.88
TPSA : 75.63 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) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.23
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 1.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.01
Solubility : 2.2 mg/ml ; 0.00985 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.531 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.36
Solubility : 0.974 mg/ml ; 0.00437 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 1142-20-7 ]

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 [ 1142-20-7 ]

* 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 [ 1142-20-7 ]
  • Downstream synthetic route of [ 1142-20-7 ]

[ 1142-20-7 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 6066-82-6 ]
  • [ 1142-20-7 ]
  • [ 3401-36-3 ]
Reference: [1] Polish Journal of Chemistry, 2005, vol. 79, # 12, p. 1909 - 1917
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2443 - 2449
[3] Liebigs Annales, 1996, # 3, p. 335 - 348
[4] Journal of Pharmaceutical Sciences, 1993, vol. 82, # 1, p. 1 - 10
[5] Chemische Berichte, 1980, vol. 113, # 11, p. 3511 - 3516
[6] Dalton Transactions, 2006, # 1, p. 137 - 148
[7] Chemistry Letters, 1985, p. 123 - 126
[8] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 7, p. 2409 - 2418
[9] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 7, p. 989 - 998
[10] Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2841 - 2845
[11] Bioorganic & Medicinal Chemistry Letters, 1998, vol. 8, # 23, p. 3343 - 3346
[12] Chemistry - A European Journal, 2004, vol. 10, # 16, p. 3879 - 3890
[13] Tetrahedron Letters, 2008, vol. 49, # 48, p. 6885 - 6888
[14] Biochimie, 2013, vol. 95, # 6, p. 1120 - 1126
[15] Tetrahedron, 2013, vol. 69, # 2, p. 551 - 558
[16] Chemistry - A European Journal, 2013, vol. 19, # 48, p. 16256 - 16262
[17] Organic Preparations and Procedures International, 2014, vol. 46, # 4, p. 370 - 375
[18] Organic and Biomolecular Chemistry, 2016, vol. 14, # 47, p. 11125 - 11136
  • 2
  • [ 1142-20-7 ]
  • [ 3401-36-3 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1661 - 1664
  • 3
  • [ 1142-20-7 ]
  • [ 90704-86-2 ]
  • [ 3401-36-3 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984, vol. 33, p. 1067 - 1070[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984, # 5, p. 1163 - 1165
  • 4
  • [ 1142-20-7 ]
  • [ 3401-36-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2364 - 2367
  • 5
  • [ 1142-20-7 ]
  • [ 75513-55-2 ]
  • [ 3401-36-3 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 15, p. 1467 - 1468
  • 6
  • [ 1142-20-7 ]
  • [ 57296-03-4 ]
  • [ 3401-36-3 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 41, p. 4451 - 4454
  • 7
  • [ 74124-79-1 ]
  • [ 1142-20-7 ]
  • [ 3401-36-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5559 - 5562
  • 8
  • [ 4515-23-5 ]
  • [ 2304-94-1 ]
  • [ 1142-20-7 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 33, p. 4783 - 4786
[2] Tetrahedron Letters, 1990, vol. 31, # 33, p. 4783 - 4786
[3] Tetrahedron Letters, 1990, vol. 31, # 33, p. 4783 - 4786
  • 9
  • [ 4132-86-9 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Chemistry Letters, 1988, p. 1125 - 1128
[2] Analytical Chemistry, 2009, vol. 81, # 24, p. 10215 - 10226
[3] Patent: WO2010/148191, 2010, A2, . Location in patent: Page/Page column 45-49; 51
[4] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 11, p. 3474 - 3476
  • 10
  • [ 920285-74-1 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 12, p. 4419 - 4425
  • 11
  • [ 64562-95-4 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1992, vol. 111, # 11, p. 490 - 495
  • 12
  • [ 501-53-1 ]
  • [ 302-72-7 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 5, p. 449 - 461
  • 13
  • [ 4108-17-2 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Chemistry Letters, 1984, p. 429 - 432
[2] Chemistry Letters, 1984, p. 433 - 436
  • 14
  • [ 917-54-4 ]
  • [ 501-53-1 ]
  • [ 193091-62-2 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Synlett, 1997, vol. 1997, # 6, p. 659 - 660
  • 15
  • [ 20790-38-9 ]
  • [ 26607-51-2 ]
  • [ 1142-20-7 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1988, # 17, p. 1214 - 1216
[2] Journal of the Chemical Society, Chemical Communications, 1988, # 17, p. 1214 - 1216
  • 16
  • [ 56-85-9 ]
  • [ 1142-20-7 ]
  • [ 39537-23-0 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With hexachloroethane; triphenylphosphine In tetrahydrofuran at 0℃; for 1.5 h;
Stage #2: With potassium hydroxide In tetrahydrofuran; dichloromethane; water at 0℃; for 2 h;
Dissolve 15 mmol of triphenylphosphine with 10 ml of tetrahydrofuran, drop it into a mixed system composed of 10 mmol of carbobenzoxy-alanine (Z-Ala), 20 mmol of hexachloroethane and 10 ml of tetrahydrofuran. After reacting at 0° C. for 1.5 hours, drop it into a liquid mixture containing 18 mmol of glutamine, 20 ml of water and 40 ml of dichloromethane. While reacting, regulate pH to 13 with potassium hydroxide, the reaction temperature is 0° C., the reaction time after dropping is 2 hours. And then acidify it to regulate pH=2.0 with dilute sulfuric acid. The aqueous phase, after concentrated, reacts with hydrogen in methanol at room temperature for 15 hours. The product L-Ala-L-Gln with a yield of 65percent is obtained.
48%
Stage #1: With hexachloroethane; triphenylphosphine In toluene at 0℃; for 3 h;
Stage #2: With sodium hydroxide In water; toluene at 15℃; for 1.5 h;
In a round bottom flask, add in 10 mmol each of carbobenzoxy-alanine (Z-Ala), triphenylphosphine and hexachloroethane respectively, and then 30 ml of toluene. After reacting at 0° C. for 3 h., drop it into a liquid mixture containing 25 mmol of glutamine and 20 ml of water. While reacting, regulate pH to 12 with sodium hydroxide, the reaction temperature is 15° C., the reaction time after dropping is 1.5 hours. And then acidify it to pH=2.5 with dilute hydrochloric acid. The aqueous phase, after concentrated, reacts with hydrogen gas in methanol at room temperature for 15 hours. The product L-Ala-L-Gln with a yield of 48percent is obtained.
45%
Stage #1: With hexachloroethane; triphenylphosphine In acetonitrile at 5℃; for 1 h;
Stage #2: With sodium hydroxide; potassium carbonate In water; acetonitrile at 5℃; for 2 h;
Dissolve 30 mmol of hexachloroethane with 10 ml of acetonitrile, drop it into a mixed system composed of 10 mmol of carbobenzoxy alanine (Z-Ala), 20 ml of triphenylphosphine and 10 ml of acetonitrile.
After reacting at 5° C. for 1.0 h., drop it into 20 ml of water containing 10 mmol of glutamine.
While reacting, regulate pH to 10 with 20 mmol of sodium hydroxide and then potassium carbonate successively, the reaction temperature is 5° C., and the reaction time after dropping is 2 hours.
And then acidify it to regulate pH to 3.0 with concentrated hydrochloric acid.
The aqueous phase, after concentrated, reacts with trifluoroacetic acid at room temperature for 40 hours.
After the reaction is finished, add in 50 ml of ether, solids deposit, the product L-Ala-L-Gln is obtained with a yield of 45percent by recrystallizing the solids with 1,4-dioxane-water.
Reference: [1] Patent: US2005/233977, 2005, A1, . Location in patent: Page/Page column 4-5
[2] Patent: US2005/233977, 2005, A1, . Location in patent: Page/Page column 4
[3] Patent: US2005/233977, 2005, A1, . Location in patent: Page/Page column 5
  • 17
  • [ 1142-20-7 ]
  • [ 74-88-4 ]
  • [ 21691-41-8 ]
Reference: [1] Journal of Solution Chemistry, 1986, vol. 15, # 2, p. 99 - 108
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 8, p. 970 - 975
[3] Canadian Journal of Chemistry, 1971, vol. 49, p. 1968 - 1971
[4] Canadian Journal of Chemistry, 1977, vol. 55, p. 906 - 910
[5] Bulletin de la Societe Chimique de France, 1975, p. 793 - 799
  • 18
  • [ 1142-20-7 ]
  • [ 101-83-7 ]
  • [ 74-88-4 ]
  • [ 21691-41-8 ]
Reference: [1] Patent: US4470973, 1984, A,
  • 19
  • [ 1142-20-7 ]
  • [ 78603-91-5 ]
Reference: [1] Applied Organometallic Chemistry, 2015, vol. 29, # 10, p. 661 - 667
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1142-20-7 ]

Amino Acid Derivatives

Chemical Structure| 1145-80-8

[ 1145-80-8 ]

Z-Ser-OH

Similarity: 0.97

Chemical Structure| 28819-05-8

[ 28819-05-8 ]

(S)-Methyl 2-(((benzyloxy)carbonyl)amino)propanoate

Similarity: 0.97

Chemical Structure| 15030-72-5

[ 15030-72-5 ]

Z-Aib-OH

Similarity: 0.95

Chemical Structure| 76387-79-6

[ 76387-79-6 ]

2-(((Benzyloxy)carbonyl)amino)malonic acid

Similarity: 0.95

Chemical Structure| 68223-03-0

[ 68223-03-0 ]

Z-D-MeAla-OH

Similarity: 0.93