[ CAS No. 616-34-2 ] {[proInfo.proName]}

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Quality Control of [ 616-34-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 616-34-2 ]

SDS Specification

Alternatived Products of [ 616-34-2 ]

Product Details of [ 616-34-2 ]

CAS No. :	616-34-2	MDL No. :	MFCD03265256
Formula :	C₃H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	89.09	Pubchem ID :	-
Synonyms :

Safety of [ 616-34-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 616-34-2 ]

* 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 [ 616-34-2 ]
Downstream synthetic route of [ 616-34-2 ]

[ 616-34-2 ] Synthesis Path-Upstream 1~11

1
[ 94274-67-6 ]
[ 616-34-2 ]
[ 56426-35-8 ]
[ 94274-53-0 ]

Reference： [1] Liebigs Annalen der Chemie, 1984, # 10, p. 1641 - 1652

2
[ 21978-63-2 ]
[ 616-34-2 ]
[ 2645-02-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2 h;	General procedure: In an oven dried 25 mL R.B. flask equipped with magnetic stir bar, was loaded with TsOBt (289 mg, 1 mmol) in DCM (1 mL) followed by DIPEA (1 equiv.) was added. Then amine (1 equiv.) was added followed by 1 mL of DCM for amines and 1.5 mL of 1:3 DMF: DCM mixture for amino acid esters. The progress of the reaction was checked by TLC. After completion of the reaction, the reaction mixture was diluted with 10 mL of DCM and organic layer was washed with 5percent HCl (3.x.10 mL), 5percent NaHCO₃ (3.x.10 mL), and saturated NaCl solution (2.x.10 mL) and dried over anhydrous CaCl₂. Then it is dried in vaccuo and purified by column chromatography.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7132 - 7134

3
[ 20992-37-4 ]
[ 616-34-2 ]
[ 2645-02-5 ]

Reference： [1] European Journal of Organic Chemistry, 2013, # 13, p. 2627 - 2633

4
[ 941-55-9 ]
[ 616-34-2 ]
[ 2645-02-5 ]

Reference： [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2681 - 2691

5
[ 616-34-2 ]
[ 100-11-8 ]
[ 94226-55-8 ]
[ 53386-64-4 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 7, p. 1273 - 1276

6
[ 616-34-2 ]
[ 5680-79-5 ]

Yield	Reaction Conditions	Operation in experiment
99.5%	With thionyl chloride In methanol at -10℃; for 0.166667 h;	IIIa the compound (3g, 40mmol) dissolved in MeOH (30 ml) in, salt bath cooling to -10 °C, stirring slowly dripping SOCl₂(29 ml, 400mmol), reaction after the end of the dropping 10 min, to remove salt bath, the reaction at room temperature overnight, TLC detection reaction, concentrating under reduced pressure, then adding 20mLCH₂Cl₂, repeatedly two times concentrated under reduced pressure, the solvent turns on lathe does, drying, the obtained product 5g, the yield is 99.5percent, product without purification, used directly in the next reaction.

Reference： [1] Patent: CN105732683, 2016, A, . Location in patent: Paragraph 0122; 0123; 0124; 0125; 0126

7
[ 53267-93-9 ]
[ 616-34-2 ]
[ 37169-36-1 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364

8
[ 80-63-7 ]
[ 616-34-2 ]
[ 79068-31-8 ]

Reference： [1] Patent: US4748183, 1988, A,
[2] Patent: EP249236, 1991, B1,

9
[ 616-34-2 ]
[ 590-46-5 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 119

10
[ 223388-21-4 ]
[ 616-34-2 ]
[ 223387-75-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 24 h; Stage #2: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 12 h;	General procedure: l-Chloro-4-hydroxyisoquinoline-3-carboxylic acid (300 mg, 1.35 mmol), amino acid methyl ester (1.2 eq), PyBOP (1.2 eq) and Et₃N (1.5 mmol) were dissolved in the anhydrous DMF (5 mL) and subsequently stirred at room temperature for 24h. Upon completion of the reaction the DMF was evaporated in vacuo and the resultant residue was suspended in CH₂CI₂ (20 mL) and washed with H₂0 (2 x 10 mL). The organic phase was dried over MgS0₄, filtered and subjected to column chromatography (Biotage SNAP KP- SIL™ 25 g cartridge, eluent system: cHex/EtOAc, ratio for elution of each methyl ester is given along with characterization of final product). The obtained product was dissolved in a mixture of THF/H₂0 (1 : 1, 10 mL) and subsequently treated with LiOH H₂0 (5 eq). The reaction was stirred at room temperature for 12h. The THF was evaporated in vacuo and the remaining aqueous solution was neutralized with cone. HC1. If precipitate was formed it was filtered-off and dried in vacuo to yield the desired product. In case that no precipitate was formed, the aqueous solution was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over MgS0₄, filtered and evaporated in vacuo to yield desired product. 2-(l-Chloro-4-hydroxyisoquinoline-3-carboxamido)acetic acid (20) The desired compound (20) was obtained as a white solid (175 mg, 46percent) starting from 1- Chloro-4-hydroxyisoquinoline-3-carboxylic acid (300 mg, 1.35 mmol). 1H MR (400 MHz, DMSO-i) δ = 9.16 (t, J=6.0 Hz, 1 H, NH), 8.30 (m, 1 H, ArH) 8.24 (m, 1 H, ArH), 7.84 - 8.09 (m, 2 H, ArH) 4.02 (d, J=6.0 Hz, 2 H, CH₂) ppm, ¹³C NMR (101 MHz, DMSO- d₆) δ = 171.4, 169.6, 155.1, 139.4, 132.6, 132.5, 130.3, 129.3, 126.9, 123.8, 121.3, 41.7 ppm. Mp = 212-214 °C, HRMS (ESI-TOF) calcd for Ci₂H₉ClN₂Na0₄ [M+Na⁺] : 303.0144, found: 303.0143, FT-IR v_max (neat): 3402, 2915, 1712, 1641, 1354, 1255, 794 cm^"1.

Reference： [1] Patent: WO2015/92412, 2015, A1, . Location in patent: Page/Page column 44; 45

11
[ 1415226-40-2 ]
[ 616-34-2 ]
[ 1000025-07-9 ]

Reference： [1] Patent: WO2016/153996, 2016, A1, . Location in patent: Paragraph 0092

[ 616-34-2 ] Synthesis Path-Downstream 1~88

1
[ 31680-07-6 ]
[ 616-34-2 ]
(2<i>RS</i>,3<i>RS</i>)-2-amino-3-hydroxy-3-(4-methyl-3-nitro-phenyl)-propionic acid methyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society,1953,p. 2564,2569

2
[ 616-34-2 ]
[ 590-46-5 ]

Reference： [1]Patent: DE269751,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 11,p. 119

3
[ 64-18-6 ]
[ 616-34-2 ]
[ 3154-54-9 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 2315 - 2320
Zhurnal Obshchei Khimii,1962,vol. 32,p. 2348 - 2353
[2]ChemMedChem,2015,vol. 10,p. 1837 - 1845

4
[ 5453-99-6 ]
[ 616-34-2 ]
[ 120800-82-0 ]

Yield	Reaction Conditions	Operation in experiment
58%	at 80℃; for 12h;

Reference： [1]Kashima, Choji; Harada, Kazuo [Journal of the Chemical Society. Perkin transactions I, 1988, p. 1521 - 1526]

5
[ 931-53-3 ]
[ 20615-64-9 ]
[ 1138-80-3 ]
[ 616-34-2 ]
[ 77280-61-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 4795 - 4798

6
[ 25090-33-9 ]
[ 616-34-2 ]
((Z)-2-Formyl-5-hydroxy-pent-1-enylamino)-acetic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,1989,p. 337 - 340

7
[ 17823-69-7 ]
[ 616-34-2 ]
[ 124476-05-7 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 1015 - 1021

8
[ 6968-11-2 ]
[ 616-34-2 ]
[ 80682-07-1 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 7374 - 7376

9
[ 61925-77-7 ]
[ 616-34-2 ]
[(R)-2-tert-Butoxycarbonylamino-3-(4-methyl-benzylsulfanyl)-propionylamino]-acetic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 4283 - 4285

10
[ 94274-67-6 ]
[ 616-34-2 ]
[ 56426-35-8 ]
[ 94274-53-0 ]

Reference： [1]Liebigs Annalen der Chemie,1984,p. 1641 - 1652

11
[ 141871-02-5 ]
[ 616-34-2 ]
[ 159878-80-5 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 9051 - 9060

12
[ 616-34-2 ]
[ 156939-62-7 ]
[ 156939-69-4 ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 1181 - 1184

13
[ 616-34-2 ]
[ 1011-40-1 ]
[ 76292-83-6 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 2197 - 2200

14
[ 39608-31-6 ]
[ 616-34-2 ]
[ 15058-27-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 2404 - 2406

15
[ 19427-28-2 ]
[ 616-34-2 ]
[ 3154-54-9 ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1994,vol. 20,p. 678 - 686
Bioorganicheskaya Khimiya,1994,vol. 20,p. 1186 - 1195

16
[ 616-34-2 ]
[ 173300-84-0 ]
[ 1212-53-9 ]
1-Benzyloxycarbonyl-3,4,5,6-tetrahydropyrimidine-2-thione [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2953 - 2954

17
[ 119072-55-8 ]
[ 3479-47-8 ]
[ 616-34-2 ]
[ 183660-36-8 ]
C₇₉H₉₁N₇O₂₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 10150 - 10155

18
[ 3479-47-8 ]
[ 39687-95-1 ]
[ 616-34-2 ]
[ 183660-36-8 ]
C₇₈H₈₇N₇O₂₇ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 10150 - 10155

19
[ 39687-95-1 ]
[ 69863-36-1 ]
[ 616-34-2 ]
[ 183660-36-8 ]
C₇₈H₈₉N₇O₂₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 10150 - 10155

20
[ 33099-08-0 ]
[ 616-34-2 ]
[ 187806-94-6 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 2111 - 2113

21
[ 616-34-2 ]
[ 109-94-4 ]
[ 3154-54-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1665 - 1668
[2]Organic Letters,2019,vol. 21,p. 5269 - 5272
[3]ChemMedChem,2020

22
[ 616-34-2 ]
[ 147071-84-9 ]
1H-pyrazole-N-propyl-1-carboxamidine hydrochloride [ No CAS ]
H₂N-L-Arg^pr-Gly-OH [ No CAS ]

Reference： [1]Synthesis,1999,p. 1495 - 1499

23
[ 42417-65-2 ]
[ 616-34-2 ]
[ 221018-59-3 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 1106 - 1107

24
[ 4816-81-3 ]
[ 616-34-2 ]
Ts-l-Ala-Gly-OCH₃ [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 769 - 772

25
[ 20372-63-8 ]
[ 108-98-5 ]
[ 616-34-2 ]
[ 76-05-1 ]
Wang resin-CH₂OCO-piperazine [ No CAS ]
4-[5-benzenesulfonyl-4-((methoxycarbonylmethyl)amino)-2-nitrobenzoyl]piperazin-1-ium trifluoroacetate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2001,p. 3233 - 3246

26
[ 616-34-2 ]
[ 100-11-8 ]
[ 94226-55-8 ]
[ 53386-64-4 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 1273 - 1276

27
[ 80745-07-9 ]
[ 616-34-2 ]
(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-acetic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 1283 - 1285

28
[ 616-34-2 ]
[ 303752-38-7 ]
methyl [3-(tert-butoxycarbonylamino)bicyclo[1.1.1]pent-1-yl]carbonyl}glycinate [ No CAS ]