2-((tert-Butoxycarbonyl)(methyl)amino)propanoic acid | Carbamates

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 1~32

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 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7848 - 7859.

29
[ 874336-37-5 ]
[ 13734-31-1 ]
[ 874336-38-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

30
[ 203732-76-7 ]
[ 13734-31-1 ]
[ 874336-36-4 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

31
[ 1351469-30-1 ]
[ 13734-31-1 ]
[ 1365991-68-9 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

32
[ 1365909-41-6 ]
[ 13734-31-1 ]
[ 1365993-77-6 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8305 - 8320.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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

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

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

[ 13734-31-1 ] Synthesis Path-Downstream 1~32

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