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Quality Control of 2-((tert-Butoxycarbonyl)(methyl)amino)propanoic acid Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of 2-((tert-Butoxycarbonyl)(methyl)amino)propanoic acid

CAS No. :	13734-31-1
Formula :	C₉H₁₇NO₄
M.W :	203.24
SMILES Code :	CC(N(C(OC(C)(C)C)=O)C)C(O)=O
MDL No. :	MFCD00153297
InChI Key :	VLHQXRIIQSTJCQ-UHFFFAOYSA-N
Pubchem ID :	4436857

Safety of 2-((tert-Butoxycarbonyl)(methyl)amino)propanoic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 2-((tert-Butoxycarbonyl)(methyl)amino)propanoic acid

* 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 [ 13734-31-1 ]

[ 13734-31-1 ] Synthesis Path-Downstream 1~35

1
[ 1070-19-5 ]
[ 600-21-5 ]
[ 13734-31-1 ]

References: [1]Justus Liebigs Annalen der Chemie,1967,vol. 702,p. 188 - 196.

2
[ 1070-19-5 ]
(R)-N-Methylalanine hydrobromide [ No CAS ]
[ 13734-31-1 ]

References: [1]Journal of general chemistry of the USSR,1968,vol. 3,p. 424 - 433.
Zhurnal Obshchei Khimii,1968,vol. 38,p. 428 - 439.

3
[ 2491-20-5 ]
[ 13734-31-1 ]
[ 19914-43-3 ]

References: [1]Journal of general chemistry of the USSR,1968,vol. 3,p. 424 - 433.
Zhurnal Obshchei Khimii,1968,vol. 38,p. 428 - 439.

4
[ 13734-31-1 ]
[ 14316-06-4 ]
[ 19914-42-2 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 58 - 60.
[2]Journal of general chemistry of the USSR,1968,vol. 3,p. 424 - 433.
Zhurnal Obshchei Khimii,1968,vol. 38,p. 428 - 439.

5
[ 13734-31-1 ]
C₁₈H₃₂N₂O₇ [ No CAS ]

References: [1]Journal of Antibiotics,1995,vol. 48,p. 805 - 810.

6
[ 13734-31-1 ]
[ 41324-66-7 ]
[ 177659-55-1 ]

References: [1]Tetrahedron,1996,vol. 52,p. 6173 - 6186.

7
[ 13734-31-1 ]
Fmoc-Ile-Cl [ No CAS ]
Fmoc-D-Pip-Cl [ No CAS ]
Fmoc-L-Pip-Cl [ No CAS ]
Boc-Pro-OH, Fmoc-D-Phe-OH [ No CAS ]
[ 138797-73-6 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1843 - 1845.

8
[ 13734-31-1 ]
[ 103321-51-3 ]
[ 142635-70-9 ]
[ 138774-86-4 ]
Boc-Pro-O-(PAM)-resin, Fmoc-D-Phe-Cl [ No CAS ]
(S)-1-{(R)-1-[(2S,3S)-2-((R)-2-Amino-3-phenyl-propionylamino)-3-methyl-pentanoyl]-piperidine-2-carbonyl}-piperidine-2-carboxylic acid [(R)-2-((S)-2-hydrazinocarbonyl-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-methyl-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3905 - 3918.

9
[ 13734-31-1 ]
[ 208522-13-8 ]
N-Boc-L-Phe-PAM resin [ No CAS ]
(S)-2-((R)-2-{Methyl-[(S)-2-((R)-2-{methyl-[(S)-2-((R)-2-{methyl-[(S)-2-((R)-2-methylamino-propionylamino)-hex-5-enoyl]-amino}-propionylamino)-3-phenyl-propionyl]-amino}-propionylamino)-hex-5-enoyl]-amino}-propionylamino)-3-phenyl-propionic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,1995,vol. 117,p. 12364 - 12365.

10
[ 40298-71-3 ]
[ 84624-27-1 ]
[ 13734-31-1 ]
[ 5241-64-5 ]
Boc-Val, Boc-Phe [ No CAS ]
(3R,6S,9R,12S,15S,18S)-12-(4-Amino-butyl)-18-benzyl-6-(4-hydroxy-benzyl)-9-(1H-indol-3-ylmethyl)-15-isopropyl-2,3-dimethyl-1-oxa-2,5,8,11,14,17-hexaaza-cyclononadecane-4,7,10,13,16,19-hexaone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1146 - 1154.

11
[ 13734-31-1 ]
1-(2-amino-3,3-dimethyl-butyryl)-pyrrolidine-2-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide hydrochloride [ No CAS ]
[(R)-1-((S)-2,2-Dimethyl-1-{(S)-2-[(R)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidine-1-carbonyl}-propylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426.

12
[ 2577-90-4 ]
[ 13734-31-1 ]
methyl N-(tert-butoxycarbonyl)-N-methyl-D-alanyl-L-phenylalaninate [ No CAS ]

References: [1]Chemistry - A European Journal,2005,vol. 11,p. 6687 - 6700.

13
[ 953391-94-1 ]
[ 13734-31-1 ]
[ 953391-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethylmorpholine;; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 0.333333h;	Description 44; l,l-Dimethylethyl ((lR)-2-[3-([2-chloro-4-(5-methyl-2- furanyl)phenyl]sulfonyl}amino)-4-(methyloxy)phenyl]amino}-l-methyl-2- oxoethyl)methylcarbamate (D44)A mixture of [Lambda]/-[(l,l-dimethylethyl)oxy]carbonyl}-[Lambda]/-methyl-D-alanine (50 mg, 0.25 mmol), 4-ethylmorpholine (57 mg, 0.5 mmol), 1-hydroxybenzotriazole hydrate (36 mg, 0.3 mmol), [Lambda]/-[3-(dimethylamino)propyl]-[Lambda]/'-ethylcarbodiimide hydrochloride ( 57 mg, 0.3 mmol), and [Lambda]/-[5-amino-2-(methyloxy)phenyl]-2-chloro-4-(5-methyl-2- furanyl)benzenesulfonamide (D43) (300 mg, 0.76 mmol) in [Lambda]/,[Lambda]/-dimethylformamide (4 mL) was stirred at room temperature overnight. The mixture was diluted with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase was washed with water and brine, dried and evaporated. Purification on a SCX-2 cartridge eluting with methanol yielded the title compound (D44). MS (ES<+>) m/e 578, 580 [M+H]<+>.

References: [1]Patent: WO2007/118852,2007,A1 .Location in patent: Page/Page column 33-34.

14
[ 13734-31-1 ]
[ 609340-69-4 ]
[ 949897-50-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4447 - 4449.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5912 - 5914.

15
[ 13734-31-1 ]
[ 173437-31-5 ]

References: [1]Journal of the American Chemical Society,1995,vol. 117,p. 12364 - 12365.

16
2S-amino-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide [ No CAS ]
[ 13734-31-1 ]
[ 183556-91-4 ]

Yield	Reaction Conditions	Operation in experiment
2.3 grams (100%)	With 4-methyl-morpholine; potassium hydrogen sulphate; benzotriazol-1-ol; 1,2-dichloro-ethane; In ethyl acetate; N,N-dimethyl-formamide;	Preparation of 2S-[[2R-[N-(tert-butoxycarbonyl)-N-(methyl)amino]propionyl]amino]-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide A solution of 0.7 grams (3.3 mmol) of N-t-BOC-N-methyl-D-alanine in 5 mL of anhydrous DMF was cooled to 0 C., charged with 0.7 grams (5.0 mmol) of HOBT and 0.7 grams (3.8 mmol) of EDC and stirred for three hours. The reaction solution was then charged with a solution of 1.7 grams (3.3 mmol) of 2S-amino-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide and 1.0 grams (9.9 mmol) of 4-methylmorpholine in 5 mL of anhydrous DMF and stirred for 18 hours. The solvents were removed in vacuo and the residue was partitioned between 150 mL of ethyl acetate and 50 mL of 5% potassium hydrogen sulfate solution. The layers were separated, and the organic layer was washed with 50 mL each of saturated sodium bicarbonate solution, water, and brine, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 2.3 grams (100%) of the desired product as a white solid, m/e=711 (M+Li).
2.3 grams (100%)	With 4-methyl-morpholine; potassium hydrogen sulphate; benzotriazol-1-ol; 1,2-dichloro-ethane; In ethyl acetate; N,N-dimethyl-formamide;	Preparation of 2S-[[2R-[N-(tert-butoxycarbonyl)-N-(methyl)amino]propionyl]amino]-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide A solution of 0.7 grams (3.3 mmol) of N-t-BOC-N-methyl-D-alanine in 5 mL of anhydrous DMF was cooled to 0 C., charged with 0.7 grams (5.0 mmol) of HOBT and 0.7 grams (3.8 mmol) of EDC and stirred for three hours. The reaction solution was then charged with a solution of 1.7 grams (3.3 mmol) of 2S-amino-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3,3-dimethylbutanamide and 1.0 grams (9.9 mmol) of 4-methylmorpholine in 5 mL of anhydrous DMF and stirred for 18 hours. The solvents were removed in vacuo and the residue was partitioned between 150 mL of ethyl acetate and 50 mL of 5% potassium hydrogen sulfate solution. The layers were separated, and the organic layer was washed with 50 mL each of saturated sodium bicarbonate solution, water, and brine, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 2.3 grams (100%) of the desired product as a white solid, m/e=711 (M+Li).

References: [1]Patent: US6143788,2000,A .
[2]Patent: US6150556,2000,A .

17
2S-amino-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3S-methylpentanamide [ No CAS ]
[ 13734-31-1 ]
2S-[[2R-[N-(tert-butoxycarbonyl)-N-(methyl)amino]propionyl]amino]-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-2S-amino-3S-methylpentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.6 grams (70%)	With 4-methyl-morpholine; potassium hydrogen sulphate; benzotriazol-1-ol; 1,2-dichloro-ethane; In hexane; ethyl acetate; N,N-dimethyl-formamide;	Preparation of 2S-[[2R-[N-(tert-butoxycarbonyl)-N-(methyl)amino]propionyl]amino]-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-2S-amino-3S-methylpentanamide A solution of 0.7 grams (3.3 mmol) of N-t-BOC-N-methyl-D-alanine in 5 mL of anhydrous DMF was cooled to 0 C., charged with 0.7 grams (5.0 mmol) of HOBT and 0.7 grams (3.8 mmol) of EDC and stirred for three hours. The reaction solution was then charged with a solution of 1.7 grams (3.3 mmol) of 2S-amino-N-[2R-hydroxy-3-[[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl]-3S-methylpentanamide and 1.0 grams (9.9mmol) of 4-methylmorpholine in 5 mL of anhydrous DMF and stirred for 16 hours. The solvents were removed in vacuo and the residue was partitioned between 150 mL of ethyl acetate and 50 mL of 5% potassium hydrogen sulfate solution. The layers were separated, and the organic layer was washed with 50 mL each of saturated sodium bicarbonate solution, water, and brine, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield the crude material. Purification was accomplished using flash chromatography on silica gel using 30-50% ethyl acetate/hexane and yielded 1.6 grams (70%) of the desired product as a white solid, m/e=711 (M+Li).

References: [1]Patent: US6150556,2000,A .

18
[ 220980-30-3 ]
[ 13734-31-1 ]
[ 1005766-14-2 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 58 - 60.

19
[ 13734-31-1 ]
[ 5845-53-4 ]
[ 1005766-13-1 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 58 - 60.

20
[ 13734-31-1 ]
[ 60538-15-0 ]
[ 1005766-15-3 ]

References: [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 58 - 60.

21
[ 13734-36-6 ]
[ 13734-34-4 ]
[ 40298-71-3 ]
[ 13734-31-1 ]
[ 1021852-90-3 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 2571 - 2574.

22
[ 1071483-69-6 ]
[ 13734-31-1 ]
C₃₃H₄₆Cl₂N₄O₅ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4817 - 4822.

23
C₁₆H₁₆ClNO₂ [ No CAS ]
[ 13734-31-1 ]
[ 1047665-93-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; In tetrahydrofuran; dichloromethane;	A slightly modified reaction sequence to that described for compounds 801 and 807 can also be employed to assemble the macrocyclic framework. In this approach, the initial alkylation as done via an SN2 displacement rather than a Mitsunobu reraction. This is illustrated for the synthesis of compound 877 from the bromide derived from tether Boc-T75a (M13), cyclopropylglycine methyl ester (M14) and the protected dipeptide (M20) in an overall yield of 35%.

References: [1]Patent: US2008/194672,2008,A1 .Location in patent: Page/Page column 62.

24
[ 2133-40-6 ]
[ 13734-31-1 ]
C₁₅H₂₆N₂O₅ [ No CAS ]

References: [1]Chemical Communications,2008,p. 4174 - 4176.

25
[ 1139932-64-1 ]
[ 13734-31-1 ]
[ 1139932-73-2 ]

References: [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 777 - 784.

26
[ 1240518-17-5 ]
[ 13734-31-1 ]
[ 1240518-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	Example 71N1-({3-[(3-[(5-Chloro-2-thienyl)sulfonyl]amino}-4-hydroxy-1H-indazol-1-yl)methyl]phenyl}methyl)-N2-methyl-D-alaninamide formic acid salt; To a solution of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (39.7 mg, 0.064 mmol) in anhydrous DMF (1 mL) was added at room temperature <strong>[13734-31-1]N-Boc-N-methyl-D-alanine</strong> (11.91 mg, 0.059 mmol), followed by N,N-diisopropylethylamine (0.0306 mL, 0.176 mmol) and finally a solution of N-(1-[3-(aminomethyl)phenyl]methyl}-4-hydroxy-1H-indazol-3-yl)-5-chloro-2-thiophenesulfonamide formate salt (for a preparation see Intermediate 15) (29 mg, 0.059 mmol) in anhydrous DMF (1 mL). The reaction mixture was stirred at room temperature for 1 hour and then was partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, washed with brine-water (1:1), passed through a hydrophobic frit, and evaporated in-vacuo to yield a colourless oil. LCMS (System B) RT=3.01 min, ES+ve m/z 634/636 (M+H)+ for desired BOC protected product. This product was suspended in a solution of hydrogen chloride in 1,4-dioxane (4M, 0.5 mL) and methanol was added until the reaction was in solution. The mixture was stirred at room temperature for 18 hours and then evaporated in-vacuo to yield a colourless oil. The residual oil was dissolved in MeOH-DMSO (0.5 mL) and purified by MDAP) on OA MDAP on Sunfire C18 column, eluting with solvents A/B (A: 0.1% v/v solution of formic acid in water, B: 0.1% v/v solution of formic acid in acetonitrile) (25 min run). The appropriate fractions were combined and evaporated in-vacuo to yield the title compound as a colourless oil (15 mg, 44%). LCMS (System B) RT=1.63 min, ES+ve m/z 534/536 (M+H)+

References: [1]Patent: US2010/216860,2010,A1 .Location in patent: Page/Page column 60.

27
[ 106665-76-3 ]
[ 13734-31-1 ]
C₂₆H₃₉N₃O₆ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4332 - 4336.

28
Boc-Aba-Gly [ No CAS ]
[ 13734-31-1 ]
[ 99953-00-1 ]
[ 1345697-93-9 ]