[ CAS No. 70138-72-6 ] {[proInfo.proName]}

Name: 70138-72-6|(R)-tert-Butyl 2-carbamoylpyrrolidine-1-carboxylate|97%
Brand: Ambeed
SKU: A187778
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Quality Control of [ 70138-72-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 70138-72-6 ]

Product Details of [ 70138-72-6 ]

CAS No. :	70138-72-6	MDL No. :	MFCD03419274
Formula :	C₁₀H₁₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	214.26	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 70138-72-6 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.5
TPSA :	72.63 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) :	-7.57 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	0.05
Log Po/w (WLOGP) :	0.49
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	-0.02
Consensus Log Po/w :	0.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	24.8 mg/ml ; 0.116 mol/l
Class :	Very soluble
Log S (Ali) :	-1.13
Solubility :	15.9 mg/ml ; 0.0744 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.59
Solubility :	54.8 mg/ml ; 0.256 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

Safety of [ 70138-72-6 ]

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

Application In Synthesis of [ 70138-72-6 ]

* 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.

Upstream synthesis route of [ 70138-72-6 ]
Downstream synthetic route of [ 70138-72-6 ]

[ 70138-72-6 ] Synthesis Path-Upstream 1~5

1
[ 70138-72-6 ]
[ 62937-45-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 7, p. 2720 - 2727

2
[ 15761-39-4 ]
[ 35150-07-3 ]
[ 70138-72-6 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2531 - 2536

3
[ 37784-17-1 ]
[ 70138-72-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78℃; for 1 h; Stage #2: With ammonia In tetrahydrofuran; water at -78 - 20℃; for 2 h;	Example 1; (R)-2-Carbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester; N-Methylmorpholine (9.85 g, 97.5 mmol) and isobutyl chloroformate (13.3 g, 97.5 mmol) was added to (R)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (20.0 g, 92.9 mmol) in THF (200 mL) at -78° C. and stirred for 1 h. Ammonium hydroxide (58 mL) was added slowly as the reaction warmed up to RT and stirred for a further 2 h. The reaction mixture was partitioned between CH₂Cl₂and water. The organic extracts were washed with 1 M HCl, dried over sodium sulphate, filtered and concentrated to afford the title product (10.8 g, 54percent) as a colourless semisolid.¹H NMR (300 MHz, CDCl₃): δ (ppm) 5.91-6.13 (m, 1H), 4.17-4.30 (m, 2H), 3.37-3.48 (m, 2H), 2.10-2.18 (m, 2H), 1.84-1.96 (m, 2H), 1.45 (s, 9H).

Reference： [1] Patent: US2007/259926, 2007, A1, . Location in patent: Page/Page column 9
[2] Tetrahedron, 2009, vol. 65, # 46, p. 9536 - 9541

4
[ 73323-65-6 ]
[ 70138-72-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6672 - 6684

5
[ 15761-39-4 ]
[ 35150-07-3 ]
[ 70138-72-6 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 13, p. 2531 - 2536

[ 70138-72-6 ] Synthesis Path-Downstream 1~16

1
(R,Z)-2-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-N-methyl-pyrrolidine-1-carboximidothioic acid methyl ester [ No CAS ]
[ 70138-72-6 ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 10(R)-2-Carbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester N-Methylmorpholine (9.85 g, 97.5 mmol) and isobutyl chloroformate (13.33 g, 97.5 mmol) was added to (R)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (20.0 g, 92.9 mmol) in THF (200 mL) at -78 C. and stirred for 1 h. Ammonium hydroxide (58 mL) was added slowly as the reaction warmed up to RT and stirred for a further 2 h. The reaction mixture was partitioned between DCM and water. The organic extracts were washed with 1 M HCl, dried over sodium sulphate, filtered and concentrated to afford the title product (10.8 g, 54%) as a colourless semisolid.1H NMR (300 MHz, CDCl3): delta (ppm) 5.91-6.13 (m, 1H), 4.17-4.30 (m, 2H), 3.37-3.48 (m, 2H), 2.10-2.18 (m, 2H), 1.84-1.96 (m, 2H), 1.45 (s, 9H).

Reference： [1]Patent: US2007/259862,2007,A1 .Location in patent: Page/Page column 23

2
[ 70138-72-6 ]
[ 228244-20-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; for 1h;	Example 11(R)-2-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester The title product of Example 10 (10.81 g, 50.45 mmol) and cyanuric chloride (5.58 g, 30.3 mmol) was stirred in DMF (30 mL) for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were washed with aq. sodium carbonate, water, brine dried over sodium sulphate, filtered and concentrated to afford the title product (8.34 g, 84%) as a colourless oil.1H NMR (300 MHz, CDCl3): delta (ppm) 4.42-4.55 (m, 1H), 3.32-3.52 (m, 2H), 2.00-2.27 (m, 4H), 1.46-1.50 (m, 9H).
84%	With 1,3,5-trichloro-2,4,6-triazine; In N,N-dimethyl-formamide; for 1h;	Example 2; (R)-2-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester; To the title product of Example 1 (10.81 g, 50.45 mmol) and cyanuric chloride (5.58 g, 30.3 mmol) was stirred in DMF (30 mL) for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were washed with aq. sodium carbonate, water, brine dried over sodium sulphate, filtered and concentrated to afford the title product (8.34 g, 84%) as a colourless oil.1H NMR (300 MHz, CDCl3): delta (ppm) 4.42-4.55 (m, 1H), 3.32-3.52 (m, 2H), 200-2.27 (m, 4H), 1.46-1.50 (m, 9H).

Reference： [1]Patent: US2007/259862,2007,A1 .Location in patent: Page/Page column 23
[2]Patent: US2007/259926,2007,A1 .Location in patent: Page/Page column 9
[3]Tetrahedron,2009,vol. 65,p. 9536 - 9541
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 6672 - 6684
[5]Journal of Medicinal Chemistry,2011,vol. 54,p. 3524 - 3548

3
[ 37784-17-1 ]
[ 70138-72-6 ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 1; (R)-2-Carbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester; N-Methylmorpholine (9.85 g, 97.5 mmol) and isobutyl chloroformate (13.3 g, 97.5 mmol) was added to (R)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (20.0 g, 92.9 mmol) in THF (200 mL) at -78 C. and stirred for 1 h. Ammonium hydroxide (58 mL) was added slowly as the reaction warmed up to RT and stirred for a further 2 h. The reaction mixture was partitioned between CH2Cl2 and water. The organic extracts were washed with 1 M HCl, dried over sodium sulphate, filtered and concentrated to afford the title product (10.8 g, 54%) as a colourless semisolid.1H NMR (300 MHz, CDCl3): delta (ppm) 5.91-6.13 (m, 1H), 4.17-4.30 (m, 2H), 3.37-3.48 (m, 2H), 2.10-2.18 (m, 2H), 1.84-1.96 (m, 2H), 1.45 (s, 9H).

Reference： [1]Patent: US2007/259926,2007,A1 .Location in patent: Page/Page column 9
[2]Tetrahedron,2009,vol. 65,p. 9536 - 9541

4
[ 179688-74-5 ]
[ 70138-72-6 ]
C₃₀H₃₁ClN₆O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6880 - 6888

5
[ 73323-65-6 ]
[ 70138-72-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6672 - 6684

6
[ 70138-72-6 ]
[ 62937-45-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2720 - 2727

7
[ 70138-72-6 ]
[ 117175-41-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With Lawessons reagent; In dichloromethane; at 20℃;	Step 1; To a stirred solution <strong>[70138-72-6]Boc-D-prolinamide</strong> (2.63 g, 12.3 mmol) in CH2CI2 (25 mL) at rt was added Lawesson's reagent (2.73 g, 6.75 mmol). The mixture was stirred overnight and concentrated. The oily residue was purified by chromatography on a 40-g silica gel cartridge, eluted with a 0-20% MeOH in CH2CI2 gradient, to afford (R)-tert-butyl 2-carbamothioylpyrrolidine-1-carboxylate (2.65 g, 94%) as a tan solid. LC-MS Method 1 tR = 1.23 min, m/z = 231 , 173, 131.

Reference： [1]Patent: WO2010/141424,2010,A1 .Location in patent: Page/Page column 50-51

8
[ 420-37-1 ]
[ 70138-72-6 ]
C₁₁H₂₀N₂O₃*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3037 - 3040

9
[ 70138-72-6 ]
C₂HF₃O₂*C₅H₁₁N₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3037 - 3040

10
[ 70138-72-6 ]
C₁₀H₁₉N₃O₂*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3037 - 3040

11
[ 70138-72-6 ]
(2R)-pyrrolidine-2-carbonitrile (TFA salt) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3524 - 3548

12
[ 70138-72-6 ]
[ 1266666-45-8 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3524 - 3548

13
[ 70138-72-6 ]
[ 1266665-51-3 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3524 - 3548

14
[ 15761-39-4 ]
[ 35150-07-3 ]
[ 70138-72-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2531 - 2536

15
[ 70138-72-6 ]
[ 117175-41-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Lawessons reagent; In dichloromethane; at 20℃;	To a stirred solution Boc-D-prolinamide (50.0 g, 234.0 mmol) in CH2Cl2 (25 mL) at rt was added Lawesson's reagent (62.2 g, 140.0 mmol). The mixture was stirred overnight, then washed with NaHCO3 (sat., 500 mL). The organic layer was washed with brine, and dried over anhydrous Na2SO4. The oily residue was purified by column chromatography on silica gel, eluted with a 0-10 percent MeOH in CH2Cl2 gradient, to afford the title compound (42 g, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 9.51 (s, 1H), 9.08 (m, 1H), 4.41 (dd, J=8.4, 3.3 Hz, 1H), 3.47-3.46 (m, 1H), 3.27 (s, 1H), 2.27-2.09 (m, 1H), 1.92-1.65 (m, 3H), 1.37 (m, 9H).

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 3592; 3593

16
[ 70138-72-6 ]
[ 212009-06-8 ]

Reference： [1]Patent: US2019/192668,2019,A1

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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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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
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Health hazards
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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. 70138-72-6 ] {[proInfo.proName]}

Quality Control of [ 70138-72-6 ]

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[ 70138-72-6 ] Synthesis Path-Upstream 1~5

[ 70138-72-6 ] Synthesis Path-Downstream 1~16

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Amides

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Aliphatic Heterocycles

Pyrrolidines

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[ 70138-72-6 ]

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[ 70138-72-6 ]