[ CAS No. 79416-27-6 ] {[proInfo.proName]}

Name: 79416-27-6|Methyl 5-amino-4-oxopentanoate hydrochloride|98%
Brand: Ambeed
SKU: A298151
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Quality Control of [ 79416-27-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79416-27-6 ]

SDS Specification

Alternatived Products of [ 79416-27-6 ]

Product Details of [ 79416-27-6 ]

CAS No. :	79416-27-6	MDL No. :
Formula :	C₆H₁₂ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJYSYPVQHFNBML-UHFFFAOYSA-N
M.W :	181.62	Pubchem ID :	157921
Synonyms :		Chemical Name :	Methyl 5-amino-4-oxopentanoate hydrochloride

Calculated chemistry of [ 79416-27-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.11
TPSA :	69.39 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) :	-7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.24
Log Po/w (WLOGP) :	0.27
Log Po/w (MLOGP) :	-0.21
Log Po/w (SILICOS-IT) :	-0.01
Consensus Log Po/w :	-0.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.48
Solubility :	59.5 mg/ml ; 0.327 mol/l
Class :	Very soluble
Log S (Ali) :	-0.76
Solubility :	31.6 mg/ml ; 0.174 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.74
Solubility :	33.2 mg/ml ; 0.183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Safety of [ 79416-27-6 ]

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 [ 79416-27-6 ]

* 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 [ 79416-27-6 ]
Downstream synthetic route of [ 79416-27-6 ]

[ 79416-27-6 ] Synthesis Path-Upstream 1~7

1
[ 79416-27-6 ]
[ 52065-78-8 ]

Reference： [1] Patent: KR2016/37530, 2016, A,

2
[ 67-56-1 ]
[ 5451-09-2 ]
[ 79416-27-6 ]

Reference： [1] Acta Poloniae Pharmaceutica - Drug Research, 2003, vol. 60, # 3, p. 219 - 224
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 8, p. 1663 - 1666[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 8, p. 1796 - 1799
[4] Patent: WO2016/102347, 2016, A1, . Location in patent: Paragraph 0359
[5] Photochemical and Photobiological Sciences, 2017, vol. 16, # 11, p. 1623 - 1630

3
[ 5451-09-2 ]
[ 79416-27-6 ]

Reference： [1] Patent: US6034267, 2000, A,
[2] Patent: US2005/31541, 2005, A1,

4
[ 67-56-1 ]
[ 106-60-5 ]
[ 79416-27-6 ]

Reference： [1] Photochemistry and Photobiology, 2001, vol. 74, # 5, p. 721 - 725

5
[ 53856-93-2 ]
[ 79416-27-6 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 8, p. 1663 - 1666[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 8, p. 1796 - 1799

6
[ 109258-71-1 ]
[ 79416-27-6 ]

7
[ 114681-18-4 ]
[ 79416-27-6 ]

[ 79416-27-6 ] Synthesis Path-Downstream 1~88

1
potassium cyanate [ No CAS ]
[ 79416-27-6 ]
[ 114659-98-2 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1663 - 1666
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 1796 - 1799

2
[ 79416-27-6 ]
[ 98-59-9 ]
[ 900795-41-7 ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 528 - 533

3
[ 79416-27-6 ]
diethyl 4-(3-methoxy-3-oxopropyl)-1H-pyrrole-2,3-dicarboxylate [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 528 - 533

4
[ 79416-27-6 ]
4-(2-methoxycarbonyl-ethyl)-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-2,3-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2006,vol. 84,p. 528 - 533

5
[ 79416-27-6 ]
Gly-Gly-ALA-OMe [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1343 - 1351

6
[ 79416-27-6 ]
Gly-Gly-Gly-ALA-OMe [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 1343 - 1351

7
[ 79416-27-6 ]
3-[2-((S)-1-Amino-3-methyl-butyl)-oxazol-5-yl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

8
[ 79416-27-6 ]
3-[2-((S)-1-Amino-3-methyl-butyl)-thiazol-5-yl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

9
[ 79416-27-6 ]
[ 379691-89-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

10
[ 79416-27-6 ]
[ 379691-85-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

11
[ 79416-27-6 ]
3-[2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-thiazol-5-yl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

12
[ 79416-27-6 ]
[ 379691-90-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

13
[ 79416-27-6 ]
3-[2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-oxazol-5-yl]-propionic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

14
[ 79416-27-6 ]
3-[2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-oxazol-5-yl]-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

15
[ 79416-27-6 ]
3-[2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-thiazol-5-yl]-propionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2593 - 2596

16
[ 79416-27-6 ]
[ 321837-96-1 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

17
[ 79416-27-6 ]
5-((S)-2-Amino-propionylamino)-4-oxo-pentanoic acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

18
[ 79416-27-6 ]
5-((S)-2-Amino-propionylamino)-4-oxo-pentanoic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

19
[ 79416-27-6 ]
5-((S)-2-Amino-3-carboxy-propionylamino)-4-oxo-pentanoic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

20
[ 79416-27-6 ]
5-((S)-2-Amino-3-phenyl-propionylamino)-4-oxo-pentanoic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

21
[ 79416-27-6 ]
5-((S)-2,6-Diamino-hexanoylamino)-4-oxo-pentanoic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4738 - 4746

22
[ 53856-93-2 ]
[ 79416-27-6 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1663 - 1666
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 1796 - 1799

23
[ 109258-71-1 ]
[ 79416-27-6 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1663 - 1666
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 1796 - 1799

24
[ 123-76-2 ]
phosphorus pentasulfide [ No CAS ]
[ 79416-27-6 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1663 - 1666
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 1796 - 1799

25
[ 114681-18-4 ]
[ 79416-27-6 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1663 - 1666
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 1796 - 1799

26
[ 79416-27-6 ]
[ 203866-13-1 ]
[ 871979-17-8 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 69-70

27
[ 79416-27-6 ]
[ 83624-01-5 ]
[ 871979-27-0 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 77

28
[ 79416-27-6 ]
[ 83623-93-2 ]
[ 871978-92-6 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 52-53

29
[ 15761-39-4 ]
[ 79416-27-6 ]
[ 871979-33-8 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 80-81

30
[ 79416-27-6 ]
[ 109523-13-9 ]
[ 871980-14-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; In dichloromethane; water;	[Step 1] 5-[(1-tert-butoxycarbonyl-(2S)-octahydroindolyl)carbonylamino]levulinic acid methyl ester (1-tert-butoxycarbonyl-(2S)-octahydroindolyl)carboxylic acid (650mg, 2.4mmol), <strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (439mg, 2.4mmol), HOBt (325mg, 2.4mmol) and EDC (695mg, 3.6mmol) were dissolved in methylene chloride (50ml), triethylamine (2.0ml, 14mmol) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction with methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.0g, 100percent) as a yellow oily substance from a methylene chloride: methanol (97:3)-eluted part. 1H-NMR (CDCl3) delta: 1.12-1.73 (17H, m), 1.94-2.32 (3H, m), 2.63-2.68 (2H, m), 2.73-2.77 (2H, m), 3.67 (3H, s), 3.81-3.93 (1H, m), 4.18-4.24 (3H, m).

Reference： [1]Patent: EP1757602,2007,A1
[2]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 135-136

31
[ 871810-88-7 ]
[ 79416-27-6 ]
[ 871979-48-5 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 93

32
[ 871810-91-2 ]
[ 79416-27-6 ]
[ 871979-48-5 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 100-101

33
[ 79416-27-6 ]
[ 361483-69-4 ]
[ 871979-67-8 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 107

34
(1-tert-butoxycarbonyl-(5S)-ethoxymethyl-(2S)-pyrrolidinyl)carboxylic acid [ No CAS ]
[ 79416-27-6 ]
[ 871979-84-9 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 118-119

35
(1-tert-butoxycarbonyl-(5S)-methoxymethyl-(2S)-pyrrolidinyl)carboxylic acid [ No CAS ]
[ 79416-27-6 ]
[ 871979-99-6 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 127-128

36
[ 871980-93-7 ]
[ 79416-27-6 ]
[ 871980-96-0 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 192-193

37
[ 871981-53-2 ]
[ 79416-27-6 ]
[ 871981-54-3 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 227-228

38
[ 79416-27-6 ]
[ 75176-20-4 ]
[ 871979-07-6 ]

Reference： [1]Patent: WO2005/121135,2005,A1 .Location in patent: Page/Page column 61-62

39
pyrrolidine-1,2-dicarboxylic acid 2-tert-butyl ester 1-(2,5-dioxo-pyrrolidin-1-yl)-ester [ No CAS ]
[ 79416-27-6 ]
2-(4-Methoxycarbonyl-2-oxo-butylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In N,N-dimethyl-formamide;	E. 2-(4-Methoxycarbonyl-2-oxo-butylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester Pyrrolidine-1,2-dicarboxylic acid 2-tert-butyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester (1.03 g, 3.3 mmol) was dissolved in DMF (30 mL) and <strong>[79416-27-6]5-amino-4-oxo-pentanoic acid methyl ester hydrochloride</strong> salt (0.60 g, 3.3 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Triethylamine was added and stirring continued overnight (ca. 16 h). The reaction was poured into water (300 mL) and extracted with ethyl acetate (370 mL). The combined organic portion was extracted with saturated aqueous sodium bicarbonate (60 mL), water (230 mL), and brine (50 mL). The organic portion was dried over magnesium sulfate and the solvent removed in vacuo. The resulting yellow oil was chromatographed on a Biotage 40S column with ethyl acetate: hexanes (4:1) to give the title compound (0.57 g, 50percent). 1H-NMR (400 MHz, CDCl3): delta4.2 (m, 3H), 3.65 (s, 3H), 3.43 (m, 1.5H), 3.35 (m, 0.5H), 2.70 (m, 2H), 2.62 (m, 2H), 2.25 (bs, 0.25H), 2.15 (bs, 0.75H), 1.88 (m, 2H), 1.70 (bs, 1H), 1.25 (bs, 9H). MS: Calc'd for C11H18N2O4 (M-BOC): 242.13. Found (M-BOC+1): 243.0.

Reference： [1]Patent: US6306887,2001,B1

40
[ 945627-32-7 ]
[ 79416-27-6 ]
[ 929630-72-8 ]

Yield	Reaction Conditions	Operation in experiment
45%	With pyridine; In dichloromethane; at 20℃; for 40h;	13-cyclohexyl-6-[[(5-methoxy-2,5-dioxopentyl)amino]carbonyl-7H-indolo[2,1-a] [2]benzazepine-10-carboxylic acid, methyl ester. 7H-indolo[2,1-a] [2]benzazepine-10-carboxylic acid, 6-(chlorocarbonyl)-13-cyclohexyl-, methyl ester (499 mg, 1.15 mMol) was dissolved in 10 ml of anhydrous dichloromethane and <strong>[79416-27-6]methyl 5-aminolevulinate hydrochloride</strong> (244 mg, 1.34 mMol) was added to the reaction mixture followed by 0.5 ml of pyridine (6.2 mMol). The reaction was stirred under nitrogen at room temperature for 40 hours. Volatiles were removed in vacuuo and the residue was partitioned between ethyl acetate and 0.1 N hydrochloric acid. The organic phase was washed with brine, dried over magnesium sulfate to yield 603 mg of crude product. The product was combined with 433 mg of a previous reaction run under the same conditions. The mixture was purified by silica column chromatography eluting with a gradient of 20percent ethyl acetate in dichloromethane to 20percent ethyl acetate in dichloromethane to yield 0.56 g (45percent) of product. 1H NMR (500 MHz, CHLOROFORM-D) delta ppm 8.28 (s, 1H) 7.87 (d, J=8.55 Hz, 1H) 7.74 (dd, J=8.55, 1.22 Hz, 1H) 7.59 (d, J=7.93 Hz, 1H) 7.43-7.56 (m, 3H) 7.38 (s, 1H) 6.71 (t, J=4.12 Hz, 1H) 5.65 (d, J=10.99 Hz, 1H) 4.31 (d, J=27.16 Hz, 2H) 4.14-4.23 (m, 1H) 3.94 (s, 3H) 3.67 (s, 3H) 2.80-2.91 (m, 1H) 2.01-2.16 (m, 3H) 1.70-2.00 (m, 3H) 1.29-1.70 (m, 6H) 1.14-1.31 (m, 2H); MS m/z 543(MH+), 560(MNH4+).

Reference： [1]Patent: US2007/185083,2007,A1 .Location in patent: Page/Page column 25

41
[ 79416-27-6 ]
[ 83624-01-5 ]
[ 871979-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; triethylamine; In methanol; dichloromethane; water;	(1-tert-butoxycarbonyl-(4R)-methoxy-(2S)-pyrrolidinyl) carboxylic acid (735 mg, 3.0 mmol), <strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (546 mg, 3.0 mmol), HOBt (405 mg, 3.0mmol) andEDC (864 mg, 4.5mmol) were dissolved in methylene chloride (35 ml), triethylamine (2.5 ml, 18 mmol) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction with methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.14 g, 100percent) as a colorless oily substance from a methylene chloride: methanol (97:3)-eluted part. 1H-NMR (CDCl3) delta: 1.38-1.51 (9H, m), 2.07-2.43 (2H, m), 2.57-2.77 (4H, m), 3.32 (3H, s), 3.47-3.52 (2H, m), 3.67 (3H, s), 3.71-4.44 (4H, m), 6.65 (1H, br s). 3-[2-(1-tert-butoxycarbonyl-(4R)-methoxy-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester

Reference： [1]Patent: EP1757602,2007,A1

42
[ 15761-39-4 ]
[ 79416-27-6 ]
[ 871979-34-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; In methanol; dichloromethane; water;	Example 26 5-[(1-tert-butoxycarbonyl-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester 1-tert-butoxycarbonyl-L-proline (645 mg, 3.0 mmol), <strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (546 mg, 3.0 mmol), HOBt (405 mg, 3.0 mmol) and EDC (864 mg, 4.5 mmol) were dissolved in methylene chloride (35 ml), triethylamine (2.5 ml, 18 mmol) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction with methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.0 g, 100percent) as a colorless oily substance from a methylene chloride: methanol (97:3)-eluted part. 1H-NMR (CDCl3) delta: 1.41-1.51 (9H, m), 1.85-2.28 (4H, m), 2.56-2.81 (4H, m), 3.41-3.51 (2H, m), 3.68 (3H, s), 4.13-4.37 (2H, m). 3-[2-(1-tert-butoxycarbonyl-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester

Reference： [1]Patent: EP1757602,2007,A1

43
[ 871810-91-2 ]
[ 79416-27-6 ]
[ 871979-58-7 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1,2-dichloro-ethane; In methanol; dichloromethane; water;	(1-tert-butoxycarbonyl-(4S)-cyclobutoxy-(2S)-pyrrolidinyl)carboxylic acid (1.0g, 3.0mmol), 5-aminolevulinic acidmethylesterhydrochloride (546mg, 3.0mmol), HOBt (405mg, 3.0mmol), and EDC (864mg, 4.5mmol) were dissolved in methylene chloride (50ml), trietyhlamine (2.5ml) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction with methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.2g, 100percent) as a yellow oily substance from a methylene chloride: methanol (97:3)-eluted part. 1H-NMR (CDCl3) delta: 1.46 (10H, br s), 1.60-1.68 (1H, m), 1.80-1.89 (2H, m), 2.06-2.47 (4H, m), 2.64-2.76 (4H, m), 3.46-3.59 (3H, m), 3.67 (3H, s), 3.85-4.36 (4H, m). 3-[2-(1-tert-butoxycarbonyl-(4S)-cyclobutoxy-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester

Reference： [1]Patent: EP1757602,2007,A1

44
(1-tert-butoxycarbonyl-(4S)-isopropoxy-(2S)-pyrrolidinyl)-carboxylic acid [ No CAS ]
[ 79416-27-6 ]
3-[2-(1-tert-butoxycarbonyl-(4S)-isopropoxy-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; In methanol; dichloromethane; water;	(1-tert-butoxycarbonyl-(4S)-isopropoxy-(2S)-pyrrolidinyl) carboxylic acid (820 mg, 3.0 mmol), <strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (546 mg, 3.0 mmol), HOBt (405 mg, 3.0 mmol) and EDC (864 mg, 4.5 mmol) were dissolved in methylene chloride (50 ml), triethylamine (2.5 ml) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction with methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.2 g, 100percent) as a colorless oily substance from a methylene chloride: methanol (97: 3) -eluted part. 1H-NMR (CDCl3) delta: 1.04 (3H, d, J = 6.1 Hz), 1.08 (3H, d, J= 6.1 Hz), 1.44 (9H, br s), 2.07-2.51 (2H, m), 2.62-2.67 (2H, m), 2.74 (2H, t, J = 6.5 Hz), 3.46-3.65 (3H, m), 3.67 (3H, s), 3.98-4.13 (2H, m), 4.19-4.39 (2H, m), 7.00-7.18 (1H, m). 3-[2-(1-tert-butoxycarbonyl-(4S)-isopropoxy-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester

Reference： [1]Patent: EP1757602,2007,A1

45
(1-tert-butoxycarbonyl-(5S)-ethoxymethyl-(2S)-pyrrolidinyl)carboxylic acid [ No CAS ]
[ 79416-27-6 ]
5-[(1-tert-butoxycarbonyl-(5S)-ethoxymethyl-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With benzotriazol-1-ol; 1,2-dichloro-ethane; In water;	[Step 6] 5-[(1-tert-butoxycarbonyl-(5S)-ethoxymethyl-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester (1-tert-butoxycarbonyl-(5S)-ethoxymethyl-(2S)-pyrrolidinyl)carboxylic acid (951mg, 3.48mmol), <strong>[79416-27-6]5-aminolevulinic acid methyl ester hydrochloride</strong> (633mg, 3.48mmol), HOBt (469mg, 3.48mmol) and EDC (1.0g, 5.2mmol) weredissolvedinmethylchloride (50ml), triethylamino (2.9ml, 20.1mmol) was added, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, followed by extraction wit methylene chloride two times. The combined extracts were dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by column chromatography using silica gel to obtain the title compound (1.3g, 93percent) as a pale yellow oily substance from a methylene chloride: methanol (97: 3)-eluted part. 1H-NMR (CDCl3) delta: 1.15-1.20 (3H, m), 1.39-1.49 (9H, m), 1.89-2.40 (4H, m), 2.62-2.69 (2H, m), 2.72-2.76 (2H, m), 3.34-3.59 (4H, m), 3.68 (3H, s), 3.98-4.31 (4H, m).

Reference： [1]Patent: EP1757602,2007,A1

46
[ 79416-27-6 ]
[ 920538-42-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With phosphoric acid; triethylamine; In water; at 0 - 20℃; for 0.166667h;	[Example 3]; Synthesis of delta-aminolevulinic acid methyl ester phosphate; A 30 g (165 mmol) portion of delta-aminolevulinic acid methyl ester hydrochloride and 20.9 g (181 mmol) of 85percent phosphoric acid were dissolved in 30 ml of purified water, and 17.5 g (173 mmol) of triethylamine was added dropwise thereto while stirring on an ice bath. After completion of the dropwise addition and subsequent stirring at room temperature for 10 minutes, 400 ml of ethanol was added thereto and stirred. The thus precipitated precipitate was recovered by suction filtration and dried at room temperature for 17 hours under a reduced pressure. A 37 g (154 mmol) portion of delta-aminolevulinic acid methyl ester phosphate was obtained at a yield of 93 molpercent. 1H-NMR (D2O 400 MHz) delta ppm: 2.68 (2H, CH2), 2.89 (2H, CH2), 3.66 (3H, CH2), 4.10 (2H, CH2) 13C-NMR (D2O, 100 MHz) delta ppm: 30 (CH2), 37 (CH2), 50 (CH2), 55 (CH3), 178 (CO), 207 (COO) The PO43- content by an ion chromatography: Theoretical value: 39.4percentMeasured value: 40percentIon chromatography analytical conditions; separation column: IonPac AS12A manufactured by Nihon Dionex Co., Ltd., eluting solution: an aqueous solution containing Na2CO3 and NaHCO3 (Na2CO3: 3.0 mmol/1, NaHCO3: 0.5 mmol/1), flow rate: 1.5 ml/min., sample injection: 25 mul, column temperature: 35°C, detector: electric conductivity detector.

Reference： [1]Patent: EP2006279,2008,A1 .Location in patent: Page/Page column 8-9

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[ 914480-55-0 ]
[ 79416-27-6 ]
[ 1166835-66-0 ]