[ CAS No. 45125-00-6 ] {[proInfo.proName]}

Name: 45125-00-6|H-D-Glu(OtBu)-OH|97%
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SKU: A164413
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Quality Control of [ 45125-00-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 45125-00-6 ]

SDS Specification

Alternatived Products of [ 45125-00-6 ]

Product Details of [ 45125-00-6 ]

CAS No. :	45125-00-6	MDL No. :	MFCD00153437
Formula :	C₉H₁₇NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	203.24	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 45125-00-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.18
TPSA :	89.62 Å²

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) :	-9.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	-2.38
Log Po/w (WLOGP) :	0.52
Log Po/w (MLOGP) :	-1.79
Log Po/w (SILICOS-IT) :	0.17
Consensus Log Po/w :	-0.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	0.8
Solubility :	1270.0 mg/ml ; 6.24 mol/l
Class :	Highly soluble
Log S (Ali) :	1.04
Solubility :	2210.0 mg/ml ; 10.9 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.66
Solubility :	44.7 mg/ml ; 0.22 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.42

Safety of [ 45125-00-6 ]

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 [ 45125-00-6 ]

* 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 [ 45125-00-6 ]
Downstream synthetic route of [ 45125-00-6 ]

[ 45125-00-6 ] Synthesis Path-Upstream 1~2

1
[ 501-53-1 ]
[ 45125-00-6 ]
[ 51644-83-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	at 0℃; for 2.5 h;	(R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid (1.00 g, 4.92 mmol) was suspended in THF (18.45ml)/Water (6.15 ml) and cooled to 0° C. using an ice bath. To the cold slurry was slowly added benzylchloroformate (0.773 mL, 5.41 mmol) and the reaction mixture was allowed to stir for 2.5 h. The slurry wasdiluted with 50 mL of EtOAc before being acidified to pH 3 using an aqueous 1N HCl solution. The crudeproduct was extracted three times with EtOAc. The organic phases were combined, dried over anhydroussodium sulfate, filtered and concentrated. The crude product was obtained as a clear oil and was subjected tosilica gel chromatography using 100percent Hexanes to 100percent ethyl acetate as eluant. The product, (R)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid, was obtained as a colorless oil (1.41 g,71percent). 1H NMR (400 MHz, chloroform-d) δ 7.44-7.29 (m, 5H), 5.53 (d, J=7.5 Hz, 1H), 5.13 (s, 2H), 4.41 (d,J=5.1 Hz, 1H), 2.56-2.30 (m, 2H), 2.21 (dd, J=13.5, 6.5 Hz, 1H), 2.06-1.88 (m, 2H), 1.45 (s, 9H).
47%	With sodium carbonate In 1,4-dioxane; water at 0 - 20℃;	To a solution of 5-tert-butyl-L-glutamate (15 g, 76 mmol) in 110 mL of water and 50 mL of dioxane was added sodium carbonate (8.0 g, 76 mmol) followed by benzyl chloroformate (13 g, 76 mmol) in 60 mL of dioxane at 0°C for 3 hours. After stirring at room temperature overnight, the mixture was extracted with ethyl acetate (50 L2) . The aqueous layer was acidified to pH 2 with 6N hydrochloric acid and extracted with ethyl acetate (50 mL3) . The organic layer was washed with brine and dried over sodium sulfate, filtered and concentrated to give N-benzyloxycarbonyl-5- ert-butyl-L-glutamate (12 g, yield 47percent) as yellow oil. (1275) ¹H-NMR (CDCI3, 300MHz): δ 7.35 (br s, 5H) , 5.76 (d, 1H, J=7.2 Hz), 5.12 (s, 2H) , 4.41-4.38 (m, 1H) , 2.43-2.35 (m, 2H) , 2.24- 2.11 (m, 1H) , 2.03-1.96 (m, 1H) 1.44 (s, 9H) .

Reference： [1] Patent: US9308236, 2016, B2, . Location in patent: Page/Page column 701; 702
[2] Patent: WO2017/73797, 2017, A1, . Location in patent: Paragraph 0208

2
[ 28920-43-6 ]
[ 45125-00-6 ]
[ 104091-08-9 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 24, p. 4590 - 4594

[ 45125-00-6 ] Synthesis Path-Downstream 1~27

1
[ 28920-43-6 ]
[ 45125-00-6 ]
[ 104091-08-9 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 4590 - 4594

2
[ 117-08-8 ]
[ 45125-00-6 ]
TCP-D-Glu(OBu-t)-OH [ No CAS ]

Reference： [1]Synthesis,2001,p. 1313 - 1320

3
[ 32315-10-9 ]
[ 45125-00-6 ]
α-L-glutamic acid-γ-(tert-butyl)ester N-carboxy anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.8%	In tetrahydrofuran; at 20℃; for 2.0h;	Example 1; Step a; Preparation of L-alpha-Glu-NCA-gamma-tBu ester; 40.17 g of triphosgene (0.135 mol; phosgene/L-Glu-gamma-tBu ester 2.74/1) and 862.5 mL of THF were placed under nitrogen into a 1 L jacketed reactor, equipped with mechanical stirrer. The reactor was thermostated at 20 C. and the mixture was stirred until complete dissolution of triphosgene (a few minutes are necessary), thereafter 30 g of L-alpha-Glu-gamma-tBu ester (0.148 mol) were added in a single portion and quite rapidly. The resulting suspension was allowed to react for 2 hours at 20 C. At the beginning exothermicity was observed (?4 C.), then the solid dissolved as the reaction proceeded: after about 30 min a clear solution was obtained. At the end of the reaction the solvent was evaporated under reduced pressure, keeping the jacket temperature not higher than 20 C.: the distillation was quite tumultuous. The distillation was continued until a dense and oily residue was obtained, without solids (about 80 mL of residue expected). At the end of the distillation 750 mL of n-heptane were dropped in over about 15 min and the mixture was stirred under nitrogen at 20/23 C. for 1 hour until complete crystallization of the product. Usually, crystallization begins after addition of 150 mL of n-heptane. The resulting pure white solid was filtered on a buchner funnel and washed with 3×90 mL of n-heptane, then dried in the oven under dynamic vacuum at 20/25 C. for no longer than 20 hours. The solid must be used as soon as possible and must be stored under static vacuum in the presence of silica gel. Starting from 30 g of L-alpha-Glu-gamma-tBu ester, 23.3 g of L-alpha-Glu-NCA-gamma-tBu ester were obtained (68.8% yield).

Reference： [1]Patent: US2008/51603,2008,A1 .Location in patent: Page/Page column 5-6

4
[ 81-30-1 ]
[ 45125-00-6 ]
C₂₃H₁₉NO₉ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 194 - 197

5
[ 45125-00-6 ]
(R)-2-[7-((R)-1-carboxy-3-ethylcarbamoyl-propyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl]-pentanedioic acid 5-tert-butyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 194 - 197

6
[ 45125-00-6 ]
[ 1026023-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; isopentyl nitrite;N,N-dimethyl-formamide; In dichloromethane;	Sidechain protected alpha-amino acids were converted to the corresponding alpha- bromo acids by the following procedure: 5 equiv. isoamyl nitrite and 5 equiv. bromine were mixed in 1 mL / mmol CH2Cl2. The amino acid was then added to the mixture as a solid. EPO <DP n="156"/>The first portion was added slowly and initiates the evolution of a gas (if no gas evolution is observed a few drops of DMF are added to help initiate the reaction), after which the remaining amino acid was added more quickly. Five minutes after the addition was complete, gas evolution was finished and the solution concentrated in vacuo. The residue was dissolved in ethyl acetate (20mL/mmol) and was washed with 0.5 M sodium thiosulfate / 1% HCl three times then 2M HCl three times. The organic phase was dried over sodium sulfate and evaporated under reduced pressure.

Reference： [1]Patent: WO2008/58016,2008,A2 .Location in patent: Page/Page column 154-155; 175

7
[ 45125-00-6 ]
[ 1357450-98-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

8
[ 45125-00-6 ]
[ 1354578-60-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

9
[ 45125-00-6 ]
[ 1354578-61-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

10
[ 45125-00-6 ]
[ 1354578-62-3 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

11
[ 45125-00-6 ]
[ 1354577-98-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

12
[ 45125-00-6 ]
[ 1939-99-7 ]
[ 1357450-88-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water; sodium hydroxide; In 1,4-dioxane; for 24.0h;pH 8-9;	(0078) (0079) To a mixture of <strong>[45125-00-6]H-<strong>[45125-00-6]D-Glu(OtBu)-OH</strong></strong> x H2O (1.0 g, 4.5 mmol), aqueous 1M NaOH (4.5 mL, 4.5 mmol), dioxane (30 mL) and water (15 mL) was added a solution of Bzls-chloride (4.9 g, 25.8 mmol) in 30 portions over 24 h. The pH was maintained between 8-9 by addition of aqueous 1M NaOH. Stirring was continued until no more starting material was detected by TLC. The solvent was evaporated in vacuo and the residue portioned between ethyl acetate and aqueous 5 % KHSO4. The organic layer was washed with aqueous 5 % KHSO4 and brine, dried over Na2SO4, and evaporated in vacuo to afford the title compound. Yield: 1.6 g (100 %, white solid). HPLC: 66.5 % B HPLC 1; MS calc.: 357.1, found 355.8 (M-H)-

Reference： [1]Patent: EP2655399,2017,B1 .Location in patent: Paragraph 0078; 0779
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1171 - 1180

13
[ 45125-00-6 ]
(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid [ No CAS ]

Reference： [1]Patent: US9308236,2016,B2

14
[ 501-53-1 ]
[ 45125-00-6 ]
[ 51644-83-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	In tetrahydrofuran; water; at 0℃; for 2.5h;	<strong>[45125-00-6](R)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid</strong> (1.00 g, 4.92 mmol) was suspended in THF (18.45ml)/Water (6.15 ml) and cooled to 0 C. using an ice bath. To the cold slurry was slowly added benzylchloroformate (0.773 mL, 5.41 mmol) and the reaction mixture was allowed to stir for 2.5 h. The slurry wasdiluted with 50 mL of EtOAc before being acidified to pH 3 using an aqueous 1N HCl solution. The crudeproduct was extracted three times with EtOAc. The organic phases were combined, dried over anhydroussodium sulfate, filtered and concentrated. The crude product was obtained as a clear oil and was subjected tosilica gel chromatography using 100% Hexanes to 100% ethyl acetate as eluant. The product, (R)-2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid, was obtained as a colorless oil (1.41 g,71%). 1H NMR (400 MHz, chloroform-d) delta 7.44-7.29 (m, 5H), 5.53 (d, J=7.5 Hz, 1H), 5.13 (s, 2H), 4.41 (d,J=5.1 Hz, 1H), 2.56-2.30 (m, 2H), 2.21 (dd, J=13.5, 6.5 Hz, 1H), 2.06-1.88 (m, 2H), 1.45 (s, 9H).
47%	With sodium carbonate; In 1,4-dioxane; water; at 0 - 20℃;	To a solution of 5-tert-butyl-L-glutamate (15 g, 76 mmol) in 110 mL of water and 50 mL of dioxane was added sodium carbonate (8.0 g, 76 mmol) followed by benzyl chloroformate (13 g, 76 mmol) in 60 mL of dioxane at 0C for 3 hours. After stirring at room temperature overnight, the mixture was extracted with ethyl acetate (50 L2) . The aqueous layer was acidified to pH 2 with 6N hydrochloric acid and extracted with ethyl acetate (50 mL3) . The organic layer was washed with brine and dried over sodium sulfate, filtered and concentrated to give N-benzyloxycarbonyl-5- ert-butyl-L-glutamate (12 g, yield 47%) as yellow oil. (1275) 1H-NMR (CDCI3, 300MHz): delta 7.35 (br s, 5H) , 5.76 (d, 1H, J=7.2 Hz), 5.12 (s, 2H) , 4.41-4.38 (m, 1H) , 2.43-2.35 (m, 2H) , 2.24- 2.11 (m, 1H) , 2.03-1.96 (m, 1H) 1.44 (s, 9H) .

Reference： [1]Patent: US9308236,2016,B2 .Location in patent: Page/Page column 701; 702
[2]Patent: WO2017/73797,2017,A1 .Location in patent: Paragraph 0208

15
[ 501-53-1 ]
[ 45125-00-6 ]
[ 140837-98-5 ]

Reference： [1]Patent: US9308236,2016,B2

16
[ 45125-00-6 ]
N-benzyloxycarbonyl-5-tert-butyl L-glutamate hexyl ester [ No CAS ]

Reference： [1]Patent: WO2017/73797,2017,A1

17
[ 45125-00-6 ]
5-tert-butyl L-glutamate hexyl ester [ No CAS ]

Reference： [1]Patent: WO2017/73797,2017,A1

18
[ 45125-00-6 ]
N-docosanoyl-5-tert-butyl L-glutamate hexyl ester [ No CAS ]

Reference： [1]Patent: WO2017/73797,2017,A1

19
[ 45125-00-6 ]
N-docosanoyl-L-glutamic acid hexyl ester [ No CAS ]

Reference： [1]Patent: WO2017/73797,2017,A1

20
[ 42855-00-5 ]
[ 45125-00-6 ]
C₁₉H₂₆N₂O₁₀ [ No CAS ]