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[ CAS No. 14296-92-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 14296-92-5
Chemical Structure| 14296-92-5
Structure of 14296-92-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 14296-92-5 ]

CAS No. :14296-92-5 MDL No. :MFCD00057234
Formula : C12H20N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :CMSBRKBRYYDCFQ-QMMMGPOBSA-N
M.W : 272.30 Pubchem ID :11673468
Synonyms :

Calculated chemistry of [ 14296-92-5 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 70.98
TPSA : 95.94 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) : -7.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 0.21
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : -0.17
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.43
Solubility : 10.2 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (Ali) : -2.16
Solubility : 1.9 mg/ml ; 0.00696 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.77
Solubility : 45.8 mg/ml ; 0.168 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.81

Safety of [ 14296-92-5 ]

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 [ 14296-92-5 ]

* 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.

  • Downstream synthetic route of [ 14296-92-5 ]

[ 14296-92-5 ] Synthesis Path-Downstream   1~85

  • 2
  • H-Gly-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Gly-Gly-NHOBzl [ No CAS ]
  • 3
  • [ 1842-55-3 ]
  • [ 14296-92-5 ]
  • t-BuOCO-Gly-L-Pro-Gly-Gly-OCH2Ph [ No CAS ]
  • 4
  • H-Leu-Ala-NHOBzl*HCl [ No CAS ]
  • [ 14296-92-5 ]
  • [ 124169-15-9 ]
  • 5
  • [ 27454-43-9 ]
  • [ 14296-92-5 ]
  • Nα-tert-butoxycarbonylglycyl-L-prolyl-Nε-tosyl-L-lysine methyl ester [ No CAS ]
  • 7
  • H-Arg(NO2)-4-hydroxypiperidine [ No CAS ]
  • [ 14296-92-5 ]
  • [ 134303-80-3 ]
  • 8
  • H-Pro-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Pro-Gly-NHOBzl [ No CAS ]
  • 9
  • H-Ser-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Ser-Gly-NHOBzl [ No CAS ]
  • 10
  • H-Glu-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Glu-Gly-NHOBzl [ No CAS ]
  • 11
  • H-Ile-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Ile-Gly-NHOBzl [ No CAS ]
  • 12
  • H-Lys-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Lys-Gly-NHOBzl [ No CAS ]
  • 13
  • H-Leu-GABA-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Leu-GABA-NHOBzl [ No CAS ]
  • 14
  • H-Leu-Val-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-Leu-Val-NHOBzl [ No CAS ]
  • 15
  • H-Phe-Gly-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • [ 124169-17-1 ]
  • 16
  • H-Leu-β-Ala-NHOBzl*HCl [ No CAS ]
  • [ 14296-92-5 ]
  • [ 137022-77-6 ]
  • 17
  • H-Leu-D-Ala-NHOBzl [ No CAS ]
  • [ 14296-92-5 ]
  • [ 124169-15-9 ]
  • 18
  • H-D-Leu-Gly-NHOBzl*HCl [ No CAS ]
  • [ 14296-92-5 ]
  • [ 137022-75-4 ]
  • 19
  • [ 14296-92-5 ]
  • [ 59191-07-0 ]
  • [ 55301-08-1 ]
  • 21
  • [ 14296-92-5 ]
  • [ 73870-86-7 ]
  • [ 73870-87-8 ]
  • 22
  • [ 14296-92-5 ]
  • H-Gly-Gly-pNA*hydrochloride [ No CAS ]
  • [ 87543-97-3 ]
  • 23
  • [ 14296-92-5 ]
  • H-L-Asn-Gly-pNA*hydrochloride [ No CAS ]
  • [ 87543-96-2 ]
  • 24
  • [ 14296-92-5 ]
  • H-L-Gln-Gly-pNA*hydrochloride [ No CAS ]
  • [ 87543-99-5 ]
  • 25
  • [ 14296-92-5 ]
  • H-L-Ala-Gly-pNA*hydrochloride [ No CAS ]
  • [ 87543-98-4 ]
  • 26
  • [ 14296-92-5 ]
  • H-D-Ala-Gly-pNA*hydrochloride [ No CAS ]
  • [ 87544-00-1 ]
  • 28
  • [ 14296-92-5 ]
  • [ 76397-13-2 ]
  • 29
  • [ 3392-07-2 ]
  • [ 147-85-3 ]
  • [ 14296-92-5 ]
YieldReaction ConditionsOperation in experiment
1. Preparation of Boc-Gly-Pro-OSu. 15 g of L-proline was dissolved in 300 ml of 10% sodium bicarbonate. 150 ml of acetone and 27.2 g of Boc-Gly-OSu were added into the reaction mixture. The mixture was stirred for 5 h at RT. The mixture was washed with ether (1 x 300 ml). 500 ml of ethyl acetate was added into the aqueous layer. The pH of the mixture was adjusted to 2.4-2.5 with ice-cooled 3N HCl. The ethyl acetate layer was collected and washed with water (3 x 300 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. 21 g of the residue (Boc-Gly-Pro-OH ) and 11 g of N-hydroxysuccinimide were dissolved in 300 ml of dichloromethlene. The mixture was cooled to 00C. 17 g of 1,3-dicyclohexylcarbodiimide was added into the reaction mixture. The mixture was stirred for 1 hour at 00C. The solid was removed by filtration. The dichloromethlene solution is washed with 5% sodium bicarbonate (I x 200 ml) and water ( 3 x 200 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. Yield 23 g Boc- Gly-Pro-OSu.
With sodium hydrogencarbonate; In acetone; at 20℃; for 5h; 15 g of L-proline was dissolved in 300 ml of 10% sodium bicarbonate. 150 ml of acetone and 27.2 g of Boc-Gly-OSu were added into the reaction mixture. The mixture was stirred for 5 h at RT. The mixture was washed with ether (1×300 ml). 500 ml of ethyl acetate was added into the aqueous layer. The pH of the mixture was adjusted to 2.4-2.5 with ice-cooled 3 N HCl. The ethyl acetate layer was collected and washed with water (3×300 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. 21 g of the residue (Boc-Gly-Pro-OH) and 11 g of N-hydroxysuccinimide were dissolved in 300 ml of dichloromethylene. The mixture was cooled to 0 C. 17 g of 1,3-dicyclohexylcarbodiimide was added into the reaction mixture. The mixture was stirred for 1 hour at 0 C. The solid was removed by filtration. The dichloromethylene solution was washed with 5% sodium bicarbonate (1×200 ml) and water (3×200 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness to yield 23 g Boc-Gly-Pro-OSu.
  • 30
  • [ 95104-84-0 ]
  • [ 147-85-3 ]
  • [ 14296-92-5 ]
  • 31
  • [ 100-02-7 ]
  • [ 14296-92-5 ]
  • Boc-Gly-Pro-p-nitrophenyl ester [ No CAS ]
  • 32
  • [ 14296-92-5 ]
  • [ 145125-83-3 ]
  • [ 213017-94-8 ]
YieldReaction ConditionsOperation in experiment
93% (E) Synthesis of Boc-Gly-pro-OH Boc-Gly-Pro-OEt (4.11 g; 15.0 mmol) obtained in (D) was dissolved in MeOH (30 ml). The reaction was carried out for 1 hour after 2N-NaOH (10 ml) was added under ice cooling, and for 4 hours after the mixture was brought back to room temperature. The MeOH was distilled off under reduced pressure and the pH was adjusted to 2 with 1N-HCl The mixture was extracted three times with AcOEt. The extracts were washed with water and dried over anhydrous MgSO4, and the solvent was distilled off under reduced pressure. The residue was recrystallized from an AcOEt-n-hexane mixed solvent to give Boc-Gly-Pro-OH (3.44 g; 93%) as colorless plates. m.p. 140.5-141 C., specific rotation [alpha]D28 -75.5 (c=1.0, EtOH). TLC (developing solvent:1 CHCl3:MeOH:AcOH=80:10:5, 2 n-BuOH:AcOH:H2 O=4:1:1; color developing method:
Boc-Gly-Pro-OH The Boc-Gly-Pro-OBz (19.4 g, 0.054 mol.) was dissolved in a mixture of 100 ml H2 O and 100 ml THF. After cooling the solution to 0 C., KOH (4.8 g, 0.085 mol.) in 50 ml H2 O was added slowly. The solution was stirred for one hour. Then, the THF was removed under reduced pressure and the aqueous solution was extracted with ethyl acetate to remove the benzyl alcohol. The resulting aqueous phase was covered by 200 ml ethyl acetate and was acidified at 0 C. to about pH 2 by addition of concentrated HCl slowly (vigorously swirling the solution at the same time). The product was extracted from the aqueous phase with ethyl acetate 3*200 ml. The organic layers were combined and washed with brine 2*30 ml, and dried by Na2 SO4. Removal of the ethyl acetate gave the product Boc-Gly-Pro-OH (white solid, 12.3 g, 85%) TLC Rf=0.25 (CMA, 85:15:3) FAB-MS, observed MH+ =273. 1 H-NMR (360 MHz, DMSO-d6, 20 C.) delta 12.55 (s, 1H, carboxyl), 6.79 (s, NH-major), 4.50 (dd, 0.25H, Pro alpha-minor), 4.20 (dd, 0.71H, Pro-alpha-major), 3.81-3.62 (m, 1.7H, Gly-alpha-major) 3.47-3.33 (m, 2H, Pro-delta and Gly-alpha-minor), 2.25-2.00 (m, 1.2H, Pro-beta), 1.96-1.60 (m, 2.7H, Pro-beta and Pro-gamma), 1.36 (s, 9H, Boc).
EXAMPLE 1 A mixture of 3.5 g (0.02 m) of N-tert.butoxycarbonyl-glycerine, 5.4 g (0.04 m) of 1-hydroxybenzotriazole, 4.82 g (0.02 m) of proline, benzyl ester hydrochloride, 6 ml of N-ethylmorpholine and 50 ml of dry tetrahydrofuran was mixed with 4.12 g (0.02 m) of dicyclohexylcarbodiimide at 10 then was stirred for 1/2 hour in the cold and at room temperature for 17 hours. The mixture was filtered. The filtrate was evaporated and partitioned between ice water, dilute hydrochloric acid and ethyl acetate. The organic extract was washed with dilute hydrochloric acid, water, bicarbonate and brine. The dried extract was concentrated to leave 7.2 g of syrupy N-t-boc.-glycyl-L-proline, benzyl ester.
EXAMPLE 2 A portion (10.3g= 0.05 mole) of dicyclohexylcarbodiimide (DCC) was added dropwise under stirring at 0 C. to a solution of N-Boc-glycyl-L-proline prepared in accordance with the method described in J. Chem. Soc. (C), 954 (1969) (27.2g= 0.1 mole) in dried THF (100ml) and the reaction mixture was kept under continuous stirring for 45 minutes.
With palladium on carbon; hydrogen; In ethanol; under 760.051 Torr; for 3h; General procedure: A mixture of compound 2a (2 mmol) and Pd/C (20 w%) in ethanol (30 mL) was hydrogenated for 3 hrs at atmospheric pressure.The reaction mixture was filtered off and concentrated in vacuo. The crude was taken in toluene and concentrated again,and then in Et2O/petroleum ether and concentrated once more to give compound 3a as a glassy solid in 62% yield overtwo steps. MS (ESI, EI-) m/z = 347 (MH-).

  • 34
  • [ 14296-92-5 ]
  • [ 54793-80-5 ]
  • [ 361541-79-9 ]
  • 35
  • [ 41863-49-4 ]
  • [ 14296-92-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; Then Boc-Gly-Pro-OMe was treated by NaOH aqueous solution and the free acid Boc-Gly-Pro-OH was given.
With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 0℃; General procedure: Dried THF:H2O (1:1) was added to Boc-gly-pro-OMe (2.86 g, 10 mmol)/Boc-Leu-pro-OMe (3.42 g, 10 mmol). To this, lithium hydroxide monohydrate (0.36 g, 15 mmol) was added at 0 C and stirred for 4-5 h. The product was isolated by adding water, acidifying upto pH 3 with KHSO4 and extracted with EtOAc (3 × 35 mL). The colorless oil was dried under reduced pressure and dried over NaSO4.
  • 36
  • [ 14296-92-5 ]
  • [ 332882-89-0 ]
  • C27H48N6O8 [ No CAS ]
  • 37
  • [ 2592-95-2 ]
  • [ 14296-92-5 ]
  • (S)-1-(2-tert-Butoxycarbonylamino-acetyl)-pyrrolidine-2-carboxylic acid benzotriazol-1-yl ester [ No CAS ]
  • 38
  • [ 14296-92-5 ]
  • 5-aminolevulinic acid ethyl ester hydrochloride [ No CAS ]
  • Boc-Gly-Pro-ALA-OEt [ No CAS ]
  • 39
  • [ 593-51-1 ]
  • [ 14296-92-5 ]
  • [ 65519-31-5 ]
  • 41
  • [ 14296-92-5 ]
  • 2(S)-(acetoxyacetyl)pyrrolidine trifluoroacetic acid salt [ No CAS ]
  • [ 870753-85-8 ]
  • 42
  • [ 5680-79-5 ]
  • [ 14296-92-5 ]
  • [ 857437-12-8 ]
  • 43
  • [ 19628-56-9 ]
  • [ 14296-92-5 ]
  • [ 490040-27-2 ]
  • 44
  • [ 14296-92-5 ]
  • [ 65482-35-1 ]
  • [ 849094-30-0 ]
  • 45
  • [ 934570-22-6 ]
  • [ 14296-92-5 ]
  • C47H56N3O11P [ No CAS ]
  • 46
  • [ 4530-20-5 ]
  • Boc-(Asp(OcHex))3-Leu-Thr(Bzl)-(Asp(OcHex))2-Gly-Merrifield resin [ No CAS ]
  • [ 14296-92-5 ]
  • 47
  • [ 14296-92-5 ]
  • pseudostellarin G [ No CAS ]
  • 49
  • [ 14296-92-5 ]
  • Boc-Pro-Phe-Ser-Phe-Gly-Pro-Leu-Ala-OH [ No CAS ]
  • 50
  • [ 14296-92-5 ]
  • H-Pro-Phe-Ser-Phe-Gly-Pro-Leu-Ala-O-C6H4-NO2-p [ No CAS ]
  • 53
  • [ 14296-92-5 ]
  • [ 66143-41-7 ]
  • 54
  • [ 14296-92-5 ]
  • N,N'-bis(glycyl-prolyl-glycyl)diaminoethane [ No CAS ]
  • 55
  • [ 14296-92-5 ]
  • [ 857437-18-4 ]
  • 56
  • [ 4530-20-5 ]
  • Boc-Ala-MBHA resin [ No CAS ]
  • [ 14296-92-5 ]
  • 57
  • [ 14296-92-5 ]
  • [ 870753-89-2 ]
  • 58
  • [ 14296-92-5 ]
  • N-(glycyl-L-prolyl)-2(S)-(hydroxyacetyl)pyrrolidine trifluoroacetate [ No CAS ]
  • 59
  • [ 14296-92-5 ]
  • [ 96055-72-0 ]
  • 60
  • [ 14296-92-5 ]
  • (S)-1-(2-Acetylamino-acetyl)-pyrrolidine-2-carboxylic acid methylamide [ No CAS ]
  • 61
  • [ 14296-92-5 ]
  • [ 530103-21-0 ]
  • 62
  • [ 14296-92-5 ]
  • [ 530103-22-1 ]
  • 63
  • [ 14296-92-5 ]
  • (S)-1-(2-Amino-acetyl)-pyrrolidine-2-carboxylic acid {(S)-1-[N'-(9,10-dioxo-9,10-dihydro-anthracen-1-yl)-hydrazinocarbonyl]-ethyl}-amide; hydrobromide [ No CAS ]
  • 64
  • [ 14296-92-5 ]
  • (S)-1-(2-Amino-acetyl)-pyrrolidine-2-carboxylic acid {(S)-1-[N'-(9,10-dioxo-9,10-dihydro-anthracen-1-yl)-hydrazinocarbonyl]-2-hydroxy-ethyl}-amide; hydrobromide [ No CAS ]
  • 65
  • [ 14296-92-5 ]
  • Gly-Pro-ALA-OEt trifluoroacetate [ No CAS ]
  • 66
  • [ 14296-92-5 ]
  • H-Gly-Pro-N-isobutylGly-OMe hydrochloride [ No CAS ]
  • 69
  • [ 14296-92-5 ]
  • H-(Gly-Pro-N-isobutylGly)2-OMe hydrochloride [ No CAS ]
  • 72
  • [ 14296-92-5 ]
  • H-(Gly-Pro-N-isobutylGly)3-OMe hydrochloride [ No CAS ]
  • 75
  • [ 14296-92-5 ]
  • C60H92N10O20 [ No CAS ]
  • 76
  • [ 14296-92-5 ]
  • Boc-β-Ala-tris(carboxyethoxymethyl)aminomethane[Gly-Pro-N-isobutylGly-OMe]3 [ No CAS ]
  • 77
  • [ 4530-20-5 ]
  • Boc-Leu-OH, Boc-Arg(Ts)-OH, Boc-Ile-OH, Boc-Pro-OH, Boc-Lys(2-chlorobenzyloxycarbonyl)-OH [ No CAS ]
  • [ 14296-92-5 ]
  • 78
  • [ 14296-92-5 ]
  • [ 87925-05-1 ]
  • 79
  • [ 14296-92-5 ]
  • (S)-1-[2-(Naphthalene-2-sulfonylamino)-acetyl]-pyrrolidine-2-carboxylic acid (4-guanidino-butyl)-amide [ No CAS ]
  • 81
  • [ 14296-92-5 ]
  • H-Gly-Pro-Pro-Phe-OMe [ No CAS ]
  • 82
  • [ 14296-92-5 ]
  • Boc-Gly-Ile-Gly-Gly-Gly-Pro-Pro-Phe-OH [ No CAS ]
  • 83
  • [ 14296-92-5 ]
  • [ 361541-80-2 ]
  • 84
  • [ 14296-92-5 ]
  • [ 191537-40-3 ]
  • 85
  • [ 14296-92-5 ]
  • Ac-(Gly-Pro-Hyp)-(Gly-Nleu-Nleu)-(Gly-Pro-Hyp)-NH2 [ No CAS ]
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