[ CAS No. 167102-61-6 ]

Name: (R)-tert-Butyl (3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate
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Quality Control of [ 167102-61-6 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 167102-61-6 ]

Product Details of [ 167102-61-6 ]

CAS No. :	167102-61-6	MDL No. :	MFCD11041265
Formula :	C₁₀H₂₀N₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	248.28	Pubchem ID :	11032217
Synonyms :

Computed Properties of [ 167102-61-6 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 167102-61-6 ]

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

Application In Synthesis of [ 167102-61-6 ]

Downstream synthetic route of [ 167102-61-6 ]

[ 167102-61-6 ] Synthesis Path-Downstream 1~1

1
[ 3262-72-4 ]
[ 6638-79-5 ]
[ 167102-61-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15℃; for 1.0h;	[0117] To a solution of Boc-D-Ser-OH (5 g, 24.37 mmol) in anhydrous DCM (100 mL) at -15C were added N,O-dimethylhydroxylaminehydrochloride (2.54 g, 26.07 mmol) and N-methylmorpholine (2.87 mL, 26.07 mmol). N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (5.00 g, 26.07 mmol) was then added portionwise (5 portions) over 20min. The mixture was stirred at -15C for 40 min. A 1 M HCl solution (50 mL) was added. The mixture was extractedwith DCM (2 x 25 mL). The organic layer was washed with a saturated solution of NaHCO3 (50 mL), H2O (50 mL), driedover Na2SO4 and concentrated in vacuo to provide the tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate (5a) (5.42 g, 21.83 mmol, 89%) as a white solid.1H NMR (400 MHz, CDCl3) delta 1.44 (s, 9H), 2.65 (s, 1 H), 3.23 (s, 3H), 3.62-3.97 (m, 5H), 4.79 (s, 1 H), 5.60 (d, J = 8.4 Hz, 1H).
83%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 20.5h;pH 4.5;Cooling with ice;	Boc-D-Serine (25.5 g, 124.5 mmol, 1.0 equiv.) was dissolved intetrahydrofuran (112 niL) and N,0-dimethylhydroxylamine hydrochloride (14 g, 143.3 mmol, 1.2 equiv.) in water (112 mL) was added. While cooling in an ice bath, IN sodium hydroxide was added to bring the pH to 4.5, then sodium hydroxide (2.45 g, 61.2 mmol, 0.5 equiv.) in water (329 mL) was added to maintain pH 4.5 and a solution of N-ethyl-N-(3-dimethylaminopropyl)carbodiimide hydrochloride (27.8 g, 145.0 mmol, 1.2 equiv.) in water (281 mL) was slowly added during 30 min (the reaction was monitored by pH meter). After stirring for 20 h at r.t., the solution was saturated with sodium chloride and extracted 3x with ethyl acetate (201 mL).Combined organic extracts were concentrated to give a crude solid. The solid was dissolved in ethyl acetate with the help of the heating and hexanes were added to give a light orange solution. As the solution cooled, small colorless crystals started forming. The solution was allowed to stand at r.t. for 30 min before being placed in an ice-bath for 30 min. The resulting colorless crystals were filtered and rinsed with 10% ethyl acetate/hexanes and dried in air to afford the title compound as a shiny snow-flakes like solid (16.48 g). The filtrate was concentrated and recrystallized to give the second crop (9.03 g) as a white solid, (total 25.5 g, 83%). NMR (300 MHz, CDCI3), delta 5.56 (brs, 1H), 4.80 (brs, 1H), 3.83 - 3.78 (m, 5H), 3.23 (s, 3H), 2.52 (brs, 1H), 1.45 (s, 9H).
77%	With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15℃; for 2.16667h;Inert atmosphere;	Scheme 1Example 1N-{2-[(3S)-3-{[(4-aminophenyl)su.fo^ phenyl}- N -(methoxycarbonyl)-p-phenyl-L-phenylalaninamide ( 12)Step 1 : A^-(^/-butoxycarbonyl)-N-methoxy-iV-inethyl-D-seriDamide (1) A suspension of N-(rert-butoxycarbonyl)-D-serine (2.06 g, 10.05 mol) in dry DCM(40 ml), stirred at -15 C (ice/salt bath) under N2 atmosphere was treated with solid N,0 hydroxylamine hydrochloride ( 1.104 g, 11 mmol) followed by N-methylmorpholine ( 1.202g, 11.9 mmol). EDC (2011 mg, 10.49 mmol) was then added to the reaction flask in five equal portions over the first 40 min, after completely charged with EDC, the reaction mixture was further stirred at the same temperature for extra 1.5h. Diluted with DCM, washed with aqueous 5% KHS04 followed by saturated solution of NaHC03, dried over Na2S04 and stored under vacuum to give 1.93g (7.78 mmol, 77% yield) of the title compound as a white solid. MS : m/z= 271.1 (MNa+).

73%	With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at -15℃; for 1.5h;	(R)-2- (tert-butoxycarbonyl)-3-hydroxypropanoic acid (5.0 g, 24.4 mmol, 1.0 equiv. ) was added to a 250 mL RBF followed by CH2C12 (90 mL) and cooled to-15 C via an ice/salt water bath. Next, N, O- dimethylhydroxyl amine-HCl (2.5 g, 25.6 mmol, 1.1 equiv. ) and N methylmorpholine (2.8 mL, 25.6 mmol, 1.1 equiv) were added to the reaction flask. EDC (4.9 g, 25.6 mmol, 1.1 equiv. ) was then added to the reaction flask in 5 equal portions over the first 30 min (1 portion per 6 min). After completely charged with EDC, the reaction was allowed to stir an additional 1 h at-15 C. The reaction was quenched with ice cold 1% HCl (25 mL) and transferred to a separatory funnel with CH2Cl2 (100 mL). The mixture was washed with 1% HCl (3 x 30 mL), sat. NaHCO3 (2 x 30 mL), and sat. NaCl (1 x 30 mL). The organic layer was separated and dried over Na2S04. The solution was concentrated on a rotary evaporator and dried under vacuum to give 4.4 g (73%) of 21 as a white solid. Rif= 0. 36 (100% EtOAc); mp = 115- 116 C ; [a] D23. s-+13. 3 (c 1.00, MeOH) ; IR (KBr) 3470,3354, 2977,2943, 1703,1645, 1538,1363, 1180, 1078, 1064 cm-1; 1H NMR (500 MHz, CDCl3) No. 5.66 (br d, J= 6.0 Hz, 1H, carbamate-NH), 4.81 (br s, 1H, Boc-NH-CH), 3.82 (m, 2H, CH-CH), 3.79 (s, 3H, N-OCH3), 3.24 (s, 3H, N-CH3), 2.86 (br s, 1H, CH2-OH), 1.45 (s, 9H, t-butyl-CH3) ; 13C (125 MHz, CDC13) 8 171.1, 156. 1, 80.2, 63.9, 61.8, 52.6, 32.3, 28.5 ; LRMS (ESI-MS mlz) : Mass calcd for CloH20N2o5 [M] +, 248.28. Found 249. Spectroscopic data were consistent with the literature data for this compound.
92 g	With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15 - -10℃; for 2.0h;Inert atmosphere;	(i?)-2-((feri-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (100 gms) was added to dichloromethane (1000 ml) under nitrogen atmosphere and stirred for 10-15 min at 25-30C. Cooled the reaction mixture to -15 to -10C. N, O-Dimethylhydroxylamine hydrochloride (45.4 gms), N-methylmorpholine (123.2 gms) and l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (95.2 gms) were added and stirred the reaction mixture for 2 hr at -15 to -10C. Acidified the reaction mixture with IN hydrochloric acid solution (600 ml) and stirred for 15 min. Separated the both aqueous and organic layers. Basify the organic layer with 5% aqueous sodium bicarbonate solution and stirred for 15 min. Separated the organic and aqueous layers and distilled off the solvent completely from the organic layer under reduced pressure. Petroleum ether ( 100 ml) was added to the above obtained material at 25- 30C and stirred the reaction mixture for 60 min at same temperature. Filtered the precipitated solid and dried to get the title compound. (Yield: 92.0 gms)

Reference： [1]Patent: EP3300736,2018,A1 .Location in patent: Paragraph 0116; 0117
[2]Tetrahedron Asymmetry,2013,vol. 24,p. 1233 - 1239
[3]Patent: WO2017/180794,2017,A1 .Location in patent: Page/Page column 63
[4]Patent: WO2012/55034,2012,A1 .Location in patent: Page/Page column 44-45
[5]Journal of the American Chemical Society,2005,vol. 127,p. 6152 - 6153
[6]Patent: WO2005/42481,2005,A2 .Location in patent: Page/Page column 22; 23
[7]Journal of the American Chemical Society,2013,vol. 135,p. 12964 - 12967
[8]Tetrahedron,1995,vol. 51,p. 8121 - 8134
[9]Synthesis,1998,p. 1707 - 1709
[10]Journal of the American Chemical Society,2008,vol. 130,p. 2351 - 2364
[11]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 537 - 542
[12]Advanced Synthesis and Catalysis,2016,vol. 358,p. 34 - 40
[13]Patent: WO2019/82209,2019,A1 .Location in patent: Page/Page column 27

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H261	In contact with water releases flammable gas
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H361d	Suspected of damaging the unborn child
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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

[ CAS No. 167102-61-6 ]

Quality Control of [ 167102-61-6 ]

Related Doc. of [ 167102-61-6 ]

Product Details of [ 167102-61-6 ]

Computed Properties of [ 167102-61-6 ]

Safety of [ 167102-61-6 ]

Application In Synthesis of [ 167102-61-6 ]

[ 167102-61-6 ] Synthesis Path-Downstream 1~1

Related Functional Groups of [ 167102-61-6 ]

Amines

Aliphatic Chain Hydrocarbons

Amides

Alcohols

Precautionary Statements-General

Prevention

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Related Functional Groups of
[ 167102-61-6 ]