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Chemical Structure| 348-67-4
Chemical Structure| 348-67-4
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Product Details of [ 348-67-4 ]

CAS No. :348-67-4 MDL No. :MFCD00002622
Formula : C5H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :FFEARJCKVFRZRR-SCSAIBSYSA-N
M.W : 149.21 Pubchem ID :84815
Synonyms :
MRX-1024;D-Methionine

Calculated chemistry of [ 348-67-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.22
TPSA : 88.62 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) : -8.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -1.87
Log Po/w (WLOGP) : 0.15
Log Po/w (MLOGP) : -2.2
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : -0.61

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.68
Solubility : 709.0 mg/ml ; 4.75 mol/l
Class : Highly soluble
Log S (Ali) : 0.53
Solubility : 504.0 mg/ml ; 3.38 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.23
Solubility : 87.5 mg/ml ; 0.586 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 348-67-4 ]

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 [ 348-67-4 ]

* 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 [ 348-67-4 ]
  • Downstream synthetic route of [ 348-67-4 ]

[ 348-67-4 ] Synthesis Path-Upstream   1~39

  • 1
  • [ 348-67-4 ]
  • [ 6027-21-0 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With methyl iodide In methanol; water at 20℃; for 48 h;
Stage #2: for 15 h; Reflux
According to a literature procedure,19D-methionine (1) (25.0 g,167.5 mmol, 1 equiv) was suspended in H2O/MeOH (466 mL/66 mL), and methyl iodide (25.2 mL, 405.4 mmol, 2.4 equiv) wasadded. The resulting suspension was stirred vigorously at roomtemperature for 48 h. Then the volume of the reaction mixturewas reduced to one-third by evaporation under vacuo and alongwith this, excess of methyl iodide was also removed. Water(155 mL) was added to the remaining reaction mixture followedby NaHCO3 (14.07 g, 167.5 mmol, 1 equiv). The resulting solutionwas refluxed for 15 h and cooled to room temperature. Solventwas removed under vacuo to yield thick syrup. This was dissolvedin water (45 mL) with heating. Addition of acetone (90 mL) followedby ethanol (1000 mL) resulted in the precipitation of a whitesolid, which was filtered and dried under vacuum to give 2 aswhite solid. Yield: 9.9 g (83 mmol, 50percent). Mp 202 C. 1H NMR(300 MHz, D2O): d = 1.92–1.78 (m, 1H, 3-CH), 2.09–2.92 (m, 1H,3-CH), 3.65–3.58 (m, 2H, 4-CH2), 3.68 (dd, 3JH,H = 4.8, 3JH,H = 7.5 Hz,1H, 2-CH). 13C NMR (75 MHz, D2O): d = 32.1 (s, 3-C), 53.3 (s, 2-C),58.5 (s, 4-C), 174.5 (s, 1-C). HRMS (ESI+, MeOH): m/z = 142.0468[M+Na]+ calcd for C4H9NO3Na+ 142.0475.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5168 - 5181
[2] Tetrahedron, 1988, vol. 44, # 2, p. 637 - 642
  • 2
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  • [ 63-68-3 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 15, p. 5115 - 5117
[2] Analytical Chemistry, 2001, vol. 73, # 22, p. 5499 - 5508
[3] Analytical Chemistry, 2003, vol. 75, # 6, p. 1508 - 1513
[4] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6526 - 6533
[5] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3481 - 3484
[6] Patent: US2013/204014, 2013, A1, . Location in patent: Paragraph 0074; 0075
[7] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 7, p. 2186 - 2188
[8] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 7, p. 2186 - 2188
[9] Chinese Journal of Chemistry, 2017, vol. 35, # 7, p. 1037 - 1042
  • 3
  • [ 59-51-8 ]
  • [ 348-67-4 ]
Reference: [1] Journal of Biological Chemistry, 1944, vol. 153, p. 398
[2] Journal of the American Chemical Society, 1958, vol. 80, p. 953,954, 957
[3] Helvetica Chimica Acta, 1948, vol. 31, p. 352
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 4604
[5] Archiv der Pharmazie (Weinheim, Germany), 1957, vol. 290, p. 571,574
[6] Tetrahedron Letters, 2002, vol. 43, # 4, p. 707 - 710
[7] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
[8] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
[9] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
  • 4
  • [ 1509-92-8 ]
  • [ 348-67-4 ]
YieldReaction ConditionsOperation in experiment
1 μmol at 4℃; for 0.0166667 h; Enzymatic reaction N-d-AAase activity was measured using N-acetyl-d-methionine as a substrate. Concentration of reaction product was measured by applying a d-amino acid oxidase coupling with horse radish peroxidase. The detailed condition was as previously described [17]. Basically, N-d-AAase and N-acetyl-d-methionine were incubated at 4 ◦C. Then the mixture of d-amino acid oxidase and colorimetric solution containing peroxidase (10 U/ml), 4-aminoantipyrine (0.04 g/ml) and 0.8 l phenol was added. The OD at wavelength 520 nm was measured. One unit was defined as generation of 1 mol d-methionine in 1 min. Protein concentration was determined by the Bradford method and bovine serum albumin as the standard [32]. Kinetic parameters kcat and Km values were determined by fitting the initial rates as a function of substrate concentration to the Michaelis–Menten equation.
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 4058
[2] Journal of Biological Chemistry, 1952, vol. 194, p. 455,458
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 4604
[4] Bulletin of the Agricultural Chemical Society of Japan, 1957, vol. 21, p. 235,237
[5] Bioscience, biotechnology, and biochemistry, 1992, vol. 56, # 9, p. 1392 - 1395
[6] Process Biochemistry, 2012, vol. 47, # 12, p. 1785 - 1790
  • 5
  • [ 52811-68-4 ]
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 206 - 208
  • 6
  • [ 44978-50-9 ]
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Reference: [1] Journal of the American Chemical Society, 1931, vol. 53, p. 3493
[2] Journal of Biological Chemistry, 1938, vol. 122, p. 426
  • 7
  • [ 583-92-6 ]
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10923 - 10929
  • 8
  • [ 1152-62-1 ]
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Reference: [1] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 5323,5326
  • 9
  • [ 452-95-9 ]
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  • [ 63-68-3 ]
Reference: [1] European Journal of Organic Chemistry, 2008, # 20, p. 3506 - 3512
  • 10
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 639,642
  • 11
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Reference: [1] Journal of the American Chemical Society, 1931, vol. 53, p. 3493
  • 12
  • [ 50-00-0 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 13
  • [ 107-97-1 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 14
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 15
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 16
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  • [ 107-43-7 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 17
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  • [ 141-53-7 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 18
  • [ 454-29-5 ]
  • [ 56-40-6 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 19
  • [ 4703-38-2 ]
  • [ 348-67-4 ]
Reference: [1] Yakugaku Zasshi, 1958, vol. 78, p. 767[2] Chem.Abstr., 1958, p. 18237
[3] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
[4] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
  • 20
  • [ 10332-17-9 ]
  • [ 348-67-4 ]
  • [ 63-68-3 ]
  • [ 21691-49-6 ]
  • [ 10332-17-9 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 21
  • [ 1115-47-5 ]
  • [ 348-67-4 ]
  • [ 63-68-3 ]
  • [ 65-82-7 ]
  • [ 1509-92-8 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19310 - 19313
  • 22
  • [ 21691-49-6 ]
  • [ 348-67-4 ]
Reference: [1] Chemische Berichte, 1958, vol. 91, p. 2410,2413
[2] Yakugaku Zasshi, 1951, vol. 71, p. 718[3] Chem.Abstr., 1952, p. 1978
[4] Yakugaku Zasshi, 1951, vol. 71, p. 1277[5] Chem.Abstr., 1952, p. 5531
[6] Yakugaku Zasshi, 1953, vol. 73, p. 355[7] Chem.Abstr., 1954, p. 3259
[8] Yakugaku Zasshi, 1953, vol. 73, p. 355[9] Chem.Abstr., 1954, p. 3259
  • 23
  • [ 4703-38-2 ]
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Reference: [1] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
  • 24
  • [ 13253-44-6 ]
  • [ 348-67-4 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 1-2, p. 91 - 95
[2] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 715 - 720
[3] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 1-2, p. 91 - 95
[4] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 715 - 720
  • 25
  • [ 4434-61-1 ]
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Reference: [1] Journal of Biological Chemistry, 1948, vol. 173, p. 471,475, 476
  • 26
  • [ 10332-17-9 ]
  • [ 348-67-4 ]
Reference: [1] Chemische Berichte, 1958, vol. 91, p. 2410,2413
[2] Yakugaku Zasshi, 1951, vol. 71, p. 1277[3] Chem.Abstr., 1952, p. 5531
[4] Yakugaku Zasshi, 1951, vol. 71, p. 718[5] Chem.Abstr., 1952, p. 1978
  • 27
  • [ 23479-37-0 ]
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Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 721 - 728
[2] Tetrahedron Asymmetry, 1995, vol. 6, # 6, p. 1257 - 1260
[3] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 721 - 728
  • 28
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Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 355[2] Chem.Abstr., 1954, p. 3259
[3] Yakugaku Zasshi, 1953, vol. 73, p. 355[4] Chem.Abstr., 1954, p. 3259
  • 29
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Reference: [1] Helvetica Chimica Acta, 1949, vol. 32, p. 333,335
  • 30
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Reference: [1] Helvetica Chimica Acta, 1949, vol. 32, p. 333,335
  • 31
  • [ 55585-92-7 ]
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Reference: [1] Journal of Biological Chemistry, 1949, vol. 178, p. 503,508[2] Journal of Biological Chemistry, 1949, vol. 180, p. 201
[3] Journal of Biological Chemistry, 1949, vol. 179, p. 1173
  • 32
  • [ 67-56-1 ]
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Reference: [1] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
[2] Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 143 - 148
  • 33
  • [ 63-68-3 ]
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Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 19, p. 4529 - 4535
  • 34
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  • [ 583-92-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 21, p. 3773 - 3781
  • 35
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  • [ 348-67-4 ]
  • [ 63-68-3 ]
  • [ 65-82-7 ]
  • [ 1509-92-8 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19310 - 19313
  • 36
  • [ 348-67-4 ]
  • [ 24424-99-5 ]
  • [ 93000-03-4 ]
Reference: [1] Patent: US5994344, 1999, A,
  • 37
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  • [ 104347-13-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 8, p. 1199 - 1210
  • 38
  • [ 348-67-4 ]
  • [ 24424-99-5 ]
  • [ 5241-66-7 ]
YieldReaction ConditionsOperation in experiment
100% With sodium carbonate; citric acid In 1,4-dioxane; water (a)
Preparation of t-butoxycarbonyl-D-methionine
D-Methionine (50.3 g, 0.34 mol) was dissolved in water (700 ml) containing sodium carbonate (71.5 g, 0.675 mol).
To this solution was added a solution of di-tert-butyl dicarbonate (81.0 g, 0.37 mol) in dioxan (250 ml) and the mixture left stirring for 16 h at room temperature.
Water (1.51) was added and the solution was washed twice with diethyl ether.
The aqueous phase was acidified to pH 3 by addition of solid citric acid and the product extracted three times with ethyl acetate (500 ml).
The combined organic phases were washed successively twice with water, once with saturated brine, then were dried over magnesium sulfate.
Evaporation gave t-butoxycarbonyl-D-methionine as an oil (87.6 g, 100percent).
[α]D +19.0° (c=1percent, MeOH).
Reference: [1] Patent: US4863953, 1989, A,
[2] Journal of the Chemical Society - Series Chemical Communications, 1989, # 22, p. 1740 - 1742
[3] Journal of Organic Chemistry, 1999, vol. 64, # 14, p. 5166 - 5175
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4815 - 4830
  • 39
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Reference: [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1984, p. 2305 - 2308
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