[ CAS No. 371240-66-3 ] {[proInfo.proName]}

Name: 371240-66-3|tert-Butyl 3-mercaptopyrrolidine-1-carboxylate|97%
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3d Animation Molecule Structure of 371240-66-3

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Quality Control of [ 371240-66-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 371240-66-3 ]

SDS Specification

Alternatived Products of [ 371240-66-3 ]

Product Details of [ 371240-66-3 ]

CAS No. :	371240-66-3	MDL No. :	MFCD16036704
Formula :	C₉H₁₇NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QZVCJLUVFPPQLX-UHFFFAOYSA-N
M.W :	203.30	Pubchem ID :	13324658
Synonyms :

Calculated chemistry of [ 371240-66-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.71
TPSA :	68.34 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	1.03
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.91
Solubility :	2.5 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (Ali) :	-2.65
Solubility :	0.459 mg/ml ; 0.00226 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.11
Solubility :	15.7 mg/ml ; 0.0774 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.81

Safety of [ 371240-66-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 371240-66-3 ]

* 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 [ 371240-66-3 ]

[ 371240-66-3 ] Synthesis Path-Downstream 1~9

1
[ 371240-66-3 ]
[ 165197-50-2 ]
[ 165197-37-5 ]

Reference： [1]Journal of Antibiotics,1995,vol. 48,p. 408 - 416

2
[ 898270-98-9 ]
[ 371240-66-3 ]
tert-butyl cis-3-({2-[(2-tert-butyl-1,1-dioxo-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl}thio)pyrrolidine-1-carboxylate [ No CAS ]
tert-butyl trans-3-({2-[(2-tert-butyl-1,1-dioxo-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl}thio)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 120℃; for 0.25h;Microwave irradiation;	Example 100; fe^-Butyl 3-({2-[(2-tert-butyl-l,l-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4- 30 yl)amino]ethyl}thio)pyrrolidine-l-carboxylate2-[(2-te/t-Butyl-l,l-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]ethyl 4- methylbenzenesulfonate (150mg, 0.313mmol) was dissolved in dry MeCN (3mL) under nitrogen atmosphere. tert-Butyl 3-mercaptopyrrolidine-l-carboxylate (70mg, 0.345mmol) was EPO <DP n="245"/>added followed by potassium carbonate (217mg, 1.567mmol). The reaction mixture was heated in a microwave reactor at 120C for 15 mins. Potassium carbonate was filtered off and the reaction ixture was evaporated to dryness in a vacuumcentrifuge. The crude product was purified by preparative HPLC affording the title compound (134mg, 83.4%). The product is a 5 mixture of cis and trans isomers. 1H NMR (CDCl3, 500MHz): delta 1.47 (s, 9H), 1.73 (s, 10H), 2.05 (s, IH), 2.46-2.51 (m, 2H), 2.88 (bs, IH), 3.01-3.13 (m, 3H), 3.29 (s, IH), 3.41-3.57 (m, 2H), 5.65 (bs, IH), 7.43-7.46 (m, 3H), 7.49-7.53 (m, 2H); 13C NMR (CDCl3, 125MHz): delta 27.83, 28.73, 31.29, 32.33, 32.86, 41.74, 42.41, 43.23, 44.86, 45.09, 52.27, 52.53, 61.86, 79.79, 108.04, 125.15, 129.04, 130.04, 131.65, 134.81, 154.41, 159.66; Mass Spectrum: 10 M+ET 509.9.

Reference： [1]Patent: WO2006/73366,2006,A1 .Location in patent: Page/Page column 243-244

3
cis-tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate [ No CAS ]
trans-tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate [ No CAS ]
[ 371240-66-3 ]

Yield	Reaction Conditions	Operation in experiment
98.4%		tert-Butyl S-mercaptopyrrolidine-l-carboxylate; tert-Butyl 3-(acetylthio)pyrrolidine-l-carboxylate (200mg, 0.81mmol) was dissolved in MeOH (1OmL) and sodium methanethiolate (57mg, 0.81mmol) was added. The reaction mixture was stirred at rt for 30mins. HCl (IM solution) was added and the aqueous layer EPO <DP n="187"/>extracted with DCM. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated affording the title compund (0.163g, 98.4%). 1H NMR (500MHz, CDCl3): delta 1.44 (s, 9H), 1.68 (d, IH), 1.75-1.84 (m, IH), 2.22-2.28 (m, IH), 3.13-3.23 (m, IH), 3.30-3.40 (m, 2H), 3.47-3.57 (m, IH), 3.67-3.74 (m, IH). 5

Reference： [1]Patent: WO2006/73366,2006,A1 .Location in patent: Page/Page column 185-186

4
dppf [ No CAS ]
[ 312537-44-3 ]
ethyl acetate n-hexane [ No CAS ]
[ 371240-66-3 ]
(RS)-3-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With caesium carbonate; In toluene;	EXAMPLE 117 (RS)-3-(2-Oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester Tris(dibenzylideneacetone)dipalladium chloroform complex (14 mg, 13.5 mol) and 1,1'-bis(diphenylphosphino)ferrocene (30 mg, 54.1 mol) in degassed and dry toluene (2 ml) were stirred at room temperature until the solution turned orange (15 minutes). 6-Bromo-3-trityl-3H-benzooxazol-2-one (0.2 g, 0.44 mmol), Cs2CO3 (0.22 g, 0.68 mmol) and (RS)-<strong>[371240-66-3]3-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester</strong> (0.1 g, 0.49 mmol) in toluene (0.5 ml) were successively added. After 4 hours stirring at 100 C., the reaction mixture was cooled to room temperature and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1 then 1:1) to provide (RS)-3-(2-oxo-3-trityl-2,3-dihydro-benzooxazol-6-yl-sulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.19 g. 77%) as a white foam, MS: m/e=596.1 (M+NH4+).

Reference： [1]Patent: US2001/47031,2001,A1

5
tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate [ No CAS ]
[ 371240-66-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium methylate; In methanol; water; ethyl acetate;	EXAMPLE 123 (RS)-3-Mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester To a 0 C. solution of (RS)-3-acetylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.4 g, 5.07 mmol) in MeOH (15 ml) was added dropwise a suspension of sodium methoxide (0.61 g, 11.3 mmol) in MeOH. After 6 hours stirring at room temperature, the reaction mixture was neutralized with 1N HCl and MeOH was partially evaporated. H2O and ethylacetate were added. The aqueous phase was extracted with ethylacetate, the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to provide (RS)-3-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester (1.2 g, 100%) as a colorless oil, MS: m/e=130.1 (M-OtBu).

Reference： [1]Patent: US2001/47031,2001,A1
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 170 - 174

6
[ 31716-01-5 ]
[ 371240-66-3 ]
C₃₁H₄₉NO₆S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 170 - 174

7
[ 1147849-27-1 ]
[ 371240-66-3 ]
[ 1147849-39-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate;sodium iodide; at 20℃;	Example 24; Preparation of di-/ert-butyl-3,3'-(3,3'-disulfanediylbis(pyridine-3,2-diyl) bis(methylene))bis(sulfanediyl)dipyrrolidine- 1 -carboxylate; Delta 5; Step 1 : A mixture of 3-(terf-butylthio)-2-(chloromethyl)pyridine 1 (0.8 g, 4.1 mmol), N-Boc-aminoethanethiol (3.46 mL, 20.5 mmol), NaI (0.15 g, 1.0 mmol) and DMF (15 mL) was stirred at rt for 1 hr. Then, the reaction mixture was extracted with ethyl acetate from sat. aq. Na2CO3. The organic layer was washed with brine, concentrated and the residue was purified by column chromatography with PE:EA = 2:1 as eluent, 1.39 g oil was obtained, yield 96%.
96%	With potassium carbonate; sodium iodide; In methanol; at 20℃; for 1.0h;	Step 1 : A mixture of 3-(tert-butylthio)-2-(chloromethyl)pyridine 1 (0.8 g, 4.1 mmol), N-Boc-aminoethanethiol (3.46 mL, 20.5 mmol), NaI (0.15 g, 1.0 mmol) and DMF (15 mL) was stirred at room temperature for 1 h. Then, the reaction mixture was extracted with EA from sat. aq. Na2CO3. The organic layer was washed with brine, <n="100"/>concentrated and the residue was purified by column chromatography with PE:EA = 2: 1 as eluent, 1.39 g oil was obtained, yield 96%.

Reference： [1]Patent: WO2010/30811,2010,A2 .Location in patent: Page/Page column 83-84
[2]Patent: WO2009/55696,2009,A1 .Location in patent: Page/Page column 97-98

8
cis-[3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl 4-methylbenzenesulfonate [ No CAS ]
[ 371240-66-3 ]
tert-butyl 3-([cis-3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl}sulfanyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1-methyl-pyrrolidin-2-one; at 20℃; for 16.0h;Inert atmosphere;	Step 1: tert-Butyl 3-([cis-3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl}sulfanyl)pyrrolidine-1-carboxylate The solution of cis-[3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl 4-methylbenzenesulfonate from Example 25, Step 4 (2 g, 3.7 mmol) was stirred in N-methylpyrrolidine (40 mL). 1,8-Diazabicycloundec-7-ene (1.13 g, 7.4 mmol) and <strong>[371240-66-3]3-mercapto-pyrrolidine-1-carboxylic acid tert-butyl ester</strong> (1.13 g, 5.6 mmol) were then added to the reaction mixture. The reaction was stirred at room temperature for 16 hours. Water (200 mL) and ethyl acetate (500 mL) were added. The aqueous layer was extracted with ethyl acetate (2*500 mL). and the combined organic layers were dried and concentrated under vacuum to give the title compound as a white solid (2.6 g, 118%). LC/MS (exact mass) calculated for C28H37N5O4S2; 571.23. found (M+H+): 572.1.

Reference： [1]Patent: US2014/243312,2014,A1 .Location in patent: Paragraph 0306

9
cis-[3-(methyl-{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl 4-methylbenzenesulfonate [ No CAS ]
[ 371240-66-3 ]
tert-butyl 3-([cis-3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)cyclobutyl]methyl}sulfanyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With 1-Methylpyrrolidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20℃; for 16.0h;Inert atmosphere;	The solution of cis-[3-(methyl{7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4- yl}amino)cyclobutyl]methyl 4-methylbenzenesulfonate from Example 25, Step 4 (2 g, 3.7 mmol) was stirred in N-methylpyrrolidine (40 mL). 1 ,8-Diazabicycloundec-7-ene (1.13 g, 7.4 mmol) and 3-mercapto-pyrrolidine-1 -carboxylic acid tert-butyl ester (1.13 g, 5.6 mmol) were then added to the reaction mixture. The reaction was stirred at room temperature for 16 hours. Water (200 mL) and ethyl acetate (500 mL) were added. The aqueous layer was extracted with ethyl ace- tate (2 x 500 mL).and the combined organic layers were dried and concentrated under vacuum to give the title compound as a white solid (2.6 g, 118%). LC/MS (exact mass) calculated for C28H37N5O4S2; 571.23, found (M + H+): 572.1.

Reference： [1]Patent: WO2016/24185,2016,A1 .Location in patent: Page/Page column 101; 102

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Technical Information

• Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Dithioacetal Formation • Ester Cleavage • Ester Hydrolysis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Grignard Reagents Transform Esters into Alcohols • Hantzsch Pyridine Synthesis • Hofmann Rearrangement • Hydride Reductions • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Lawesson's Reagent • Oxidation States of Sulfur Compounds • Preparation of Amines • Radical Addition of a Thiol to an Alkene • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reduction of Disulfides to Thiols • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification

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P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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

[ CAS No. 371240-66-3 ] {[proInfo.proName]}

Quality Control of [ 371240-66-3 ]

Related Doc. of [ 371240-66-3 ]

Product Details of [ 371240-66-3 ]

Calculated chemistry of [ 371240-66-3 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 371240-66-3 ]

Application In Synthesis of [ 371240-66-3 ]

[ 371240-66-3 ] Synthesis Path-Downstream 1~9

Technical Information

Related Functional Groups of [ 371240-66-3 ]

Amides

Related Parent Nucleus of [ 371240-66-3 ]

Aliphatic Heterocycles

Pyrrolidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 371240-66-3 ]

Related Parent Nucleus of
[ 371240-66-3 ]