[ CAS No. 102195-79-9 ] {[proInfo.proName]}

Name: 102195-79-9|(2S,4S)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate|97%
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Quality Control of [ 102195-79-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 102195-79-9 ]

SDS Specification

Alternatived Products of [ 102195-79-9 ]

Product Details of [ 102195-79-9 ]

CAS No. :	102195-79-9	MDL No. :	MFCD00237541
Formula :	C₁₁H₁₉NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MZMNEDXVUJLQAF-YUMQZZPRSA-N
M.W :	245.27	Pubchem ID :	10752873
Synonyms :	N-Boc-4-hydroxy-L-proline methyl ester	Chemical Name :	(2S,4S)-1-tert-Butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Calculated chemistry of [ 102195-79-9 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	5
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.85
TPSA :	76.07 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) :	-7.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.72
Log Po/w (XLOGP3) :	0.58
Log Po/w (WLOGP) :	0.15
Log Po/w (MLOGP) :	0.22
Log Po/w (SILICOS-IT) :	-0.11
Consensus Log Po/w :	0.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.4
Solubility :	9.85 mg/ml ; 0.0402 mol/l
Class :	Very soluble
Log S (Ali) :	-1.75
Solubility :	4.36 mg/ml ; 0.0178 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.27
Solubility :	131.0 mg/ml ; 0.535 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.36

Safety of [ 102195-79-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 102195-79-9 ]

* 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 [ 102195-79-9 ]

[ 102195-79-9 ] Synthesis Path-Downstream 1~2

1
[ 1145663-09-7 ]
[ 102195-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56.2 g / triethylamine / CH₂Cl₂ / 3 h / 0 - 5 °C 2: 88.7 percent / dimethylsulfoxide / 90 °C 3: 98.4 percent / potassium carbonate / methanol / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: DIAD; PPh₃ / tetrahydrofuran / 1 h / 0 - 20 °C 2: 1N aq. NaOH / methanol / 1 h / 0 °C
	Multi-step reaction with 2 steps 1: 95 percent / PPh₃; DEAD / tetrahydrofuran 2: 95 percent / K₂CO₃ / methanol

	Multi-step reaction with 2 steps 1: 94 percent / PPh₃, DEAD 2: 95 percent / NaOMe / methanol
	Multi-step reaction with 2 steps 1: 66 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.67 h / 0 °C 2: 89 percent / aq. NaOH / methanol / 0.33 h
	With triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid In tetrahydrofuran at 0 - 30℃;	2.B Step. The compound of Step A (144. 5g, 0. 59 mol), triphenyl phosphine (200g, 0. 76 mol, 1. 29 eq), p- nitrobenzoic acid (150 g, 0. 9 mol, 1. 52 eq) and THF (2. 5 L) were mixed and cooled to 0°C. Diethyl diazodicarboxylate (120 mL, 0. 76 mol, 1. 29 eq) was added over 10 min. The reaction exotherme to 30°C and was allowed to cool to room temperature and stir overnight. The reaction was concentrated, the residue diluted with ether (1L) and the resulting suspension filtered. The filtrate was again concentrated, re-dissolved in CH2C12 and chromatographed (silica, linear gradient CH2C12 to 5% EtOAc/CH2Cl). The product cuts were combined and concentrated. The concentrate was flushed with ether then hexanes to afford a white slurry which was filtered and dried giving 218. 7g of the title compound as a white solid.
	Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran 2: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol
	Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: methanol; potassium carbonate / 1 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 0 °C 2: (methylsulfinyl)methane / 6 h / 20 - 90 °C 3: potassium carbonate; methanol / 0.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6.5 h / 0 - 20 °C / Inert atmosphere 2: Caswell No_. 744A / propan-2-one / 14 h / Reflux
	Multi-step reaction with 2 steps 1: triphenylphosphine; triethylamine; di-isopropyl azodicarboxylate / tetrahydrofuran / 6 h / 0 - 20 °C 2: Caswell No_. 744A / propan-2-one / 14 h / Reflux
	Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / -4 - 20 °C 2: anhydrous sodium carbonate; methanol / 4 h / 20 °C
	Stage #1: 1-(tert-butyl) 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate With methanesulfonyl chloride; triethylamine In dichloromethane Stage #2: With benzoic acid sodium salt In dichloromethane at 90℃; Stage #3: With potassium carbonate In methanol; dichloromethane
	Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / -4 - 20 °C 2: anhydrous sodium carbonate / methanol / 4 h / 20 °C
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: methanol; Caswell No_. 744A / 4 h / 40 °C
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 48 h / 0 - 50 °C / Inert atmosphere 2: Caswell No_. 744A / methanol / 40 h / 40 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere; Cooling with ice bath 2.1: methanol; potassium hydroxide / 0.5 h / 0 °C / Cooling with ice bath; Inert atmosphere 2.2: Inert atmosphere
	Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C 2.1: Caswell No_. 744A / N,N-dimethyl-formamide / 16 h / 70 °C 3.1: benzoic acid sodium salt / (methylsulfinyl)methane / 17 h / 90 °C 3.2: 1 h / 20 °C
	Multi-step reaction with 2 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 2 h / 0 - 25 °C / Large scale 2: sodium tetrahydridoborate
	Multi-step reaction with 2 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 2 h / 0 - 25 °C / Large scale 2: D-glucose; NADP; glucose dehydrogenase; keto reductase KRED PK₀₇₆ / aq. phosphate buffer / 20 h / 37 °C / Large scale; Enzymatic reaction

Reference： [1]Marusawa, Hiroshi; Setoi, Hiroyuki; Sawada, Akihiko; Kuroda, Akio; Seki, Jiro; Motoyama, Yukio; Tanaka, Hirokazu [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 5, p. 1399 - 1415]
[2]Eno, Kaoru; Okuno, Takayuki; Nishi, Koichi; Murakami, Yasushi; Yamada, Katsutoshi; Nakamoto, Shozo; Ono, Takashi [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 4, p. 587 - 590]
[3]Zhang, Xiaojun; Schmitt, Aaron C.; Jiang, Wen [Tetrahedron Letters, 2001, vol. 42, # 32, p. 5335 - 5338]
[4]Jordan, Stephan; Schwemler, Christoph; Kosch, Winfried; Kretschmer, Axel; Schwenner, Eckhardt; Stropp, Udo; Mielke, Burkhard [Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 681 - 686]
[5]Iso; Irie; Iwaki; Kii; Sendo; Motokawa; Nishitani [Journal of Antibiotics, 1996, vol. 49, # 5, p. 478 - 484]
[6]Current Patent Assignee: MERCK & CO INC - WO2005/87760, 2005, A1 Location in patent: Page/Page column 20
[7]Rawson, David J.; Brugier, Delphine; Harrison, Anthony; Hough, Jo; Newman, Julie; Otterburn, Joe; Maw, Graham N.; Price, Jenny; Thompson, Lisa R.; Turnpenny, Paul; Warren, Andrew N. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 12, p. 3767 - 3770]
[8]Zhao, Jielu; Bane, Susan; Snyder, James P.; Hu, Haipeng; Mukherjee, Kamalika; Slebodnick, Carla; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 24, p. 7664 - 7678]
[9]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2013/102242, 2013, A1
[10]Tressler, Caitlin M.; Zondlo, Neal J. [Journal of Organic Chemistry, 2014, vol. 79, # 12, p. 5880 - 5886]
[11]Current Patent Assignee: ZONDLO, Neal; PANDEY, Anil; TRESSLER, Caitlin - WO2014/127052, 2014, A1
[12]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2015/152068, 2015, A1
[13]Kaplaneris, Nikolaos; Koutoulogenis, Giorgos; Raftopoulou, Marianna; Kokotos, Christoforos G. [Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5464 - 5473]
[14]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2015/79417, 2015, A1
[15]Forbes, Christina R.; Pandey, Anil K.; Ganguly, Himal K.; Yap, Glenn P. A.; Zondlo, Neal J. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 7, p. 2327 - 2346]
[16]Hentzen, Nina B.; Smeenk, Linde E. J.; Witek, Jagna; Riniker, Sereina; Wennemers, Helma [Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12815 - 12820]
[17]Current Patent Assignee: ACHAOGEN INC; NUMERATE INC - WO2009/137130, 2009, A2
[18]Bonneure, Eli; De Baets, Amber; De Decker, Sam; Van den Berge, Koen; Clement, Lieven; Vyverman, Wim; Mangelinckx, Sven [International Journal of Molecular Sciences, 2021, vol. 22, # 3, p. 1 - 14]
[19]Guo, Wenxing; Gharbaoui, Tawfik; Lizza, Joseph R.; Meng, Fanfan; Wang, Yuanxian; Xin, Maoshu; Chen, Yuanpeng; Li, Jing; Chen, Cheng-Yi [Organic Process Research and Development, 2022, vol. 26, # 10, p. 2839 - 2846]
[20]Guo, Wenxing; Gharbaoui, Tawfik; Lizza, Joseph R.; Meng, Fanfan; Wang, Yuanxian; Xin, Maoshu; Chen, Yuanpeng; Li, Jing; Chen, Cheng-Yi [Organic Process Research and Development, 2022, vol. 26, # 10, p. 2839 - 2846]

2
[ 102195-79-9 ]
[ 1207853-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: triethylamine / dichloromethane / 2 h / 0 °C / Large scale 2.1: sodium azide / N,N-dimethyl-formamide / 4 h / 0 - 80 °C 3.1: lithium borohydride / tetrahydrofuran / 3 h / -30 - 20 °C 4.1: sodium hydride / acetonitrile; paraffin oil / 0.5 h / 0 °C 4.2: 5 h / 20 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 20 °C

Reference： [1]Current Patent Assignee: MISSION THERAPEUTICS LIMITED - WO2020/212351, 2020, A1

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[ 102195-79-9 ]

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H242	Heating may cause a fire
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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. 102195-79-9 ] {[proInfo.proName]}

Quality Control of [ 102195-79-9 ]

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Product Details of [ 102195-79-9 ]

Calculated chemistry of [ 102195-79-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 102195-79-9 ]

Application In Synthesis of [ 102195-79-9 ]

[ 102195-79-9 ] Synthesis Path-Downstream 1~2

Related Functional Groups of [ 102195-79-9 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

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Related Functional Groups of
[ 102195-79-9 ]