(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- Product Name
- (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- CAS No.
- 101410-18-8
- Chemical Name
- (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- Synonyms
- 1-Pyrrolidineca;BOC-(S)-Pyrrolidine-2-Thiocarboxamide;(S)-1-Boc-pyrrolidine-2-carbothioamide;N-BOC-(S)-Pyrrolidine-2-thiocarboxamide;TERT-BUTYL2(S)-THIOCARBAMOYLPYRROLIDINE-1-CARBOXYLATE;tert-butyl (S)-2-carbamothioylpyrrolidine-1-carboxylate;(S)-tert-butyl 2-thiocarbaMoylpyrrolidine-1-carboxylate;tert-butyl (2S)-2-carbamothioylpyrrolidine-1-carboxylate;2-Methyl-2-propanyl (2S)-2-carbamoyl-1-pyrrolidinecarboxylate;2R-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- CBNumber
- CB5386725
- Molecular Formula
- C10H18N2O2S
- Formula Weight
- 230.33
- MOL File
- 101410-18-8.mol
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Property
- Melting point:
- 195-199 °C(Solv: tetrahydrofuran (109-99-9))
- Boiling point:
- 339.5±52.0 °C(Predicted)
- Density
- 1.191±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 12.98±0.20(Predicted)
- Appearance
- White to off-white Solid
- InChI
- InChI=1S/C10H18N2O2S/c1-10(2,3)14-9(13)12-6-4-5-7(12)8(11)15/h7H,4-6H2,1-3H3,(H2,11,15)/t7-/m0/s1
- InChIKey
- KPAOKCBKJXBXNI-ZETCQYMHSA-N
- SMILES
- N1(C(OC(C)(C)C)=O)CCC[C@H]1C(N)=S
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B810415
- Product name
- (S)-tert-Butyl2-Carbamothioylpyrrolidine-1-carboxylate
- Packaging
- 50mg
- Price
- $130
- Updated
- 2021/12/16
- Product number
- B399
- Product name
- (S)-2-Thiocarbamoyl-pyrrolidine-1-carboxylicacidtert-butylester
- Packaging
- 250mg
- Price
- $139
- Updated
- 2021/12/16
- Product number
- CS-0047030
- Product name
- tert-Butyl(S)-2-carbamothioylpyrrolidine-1-carboxylate
- Purity
- 97.26%
- Packaging
- 1g
- Price
- $85
- Updated
- 2021/12/16
- Product number
- AS36058
- Product name
- (S)-(1-Boc)-2-carbamothioylpyrrolidine
- Purity
- 95+% ee
- Packaging
- 1g
- Price
- $265
- Updated
- 2021/12/16
- Product number
- CS-0047030
- Product name
- tert-Butyl(S)-2-carbamothioylpyrrolidine-1-carboxylate
- Purity
- 97.26%
- Packaging
- 5g
- Price
- $270
- Updated
- 2021/12/16
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties,Usage,Production
Synthesis
35150-07-3
117175-41-4
General procedure for the synthesis of tert-butyl (R)-2-thiocarboxamido pyrrolidine-1-carboxylate from N-tert-butoxycarbonyl-L-prolinamide: (S)-1-(tert-butoxycarbonyl)prolinamide (9.0 g, 42.0 mmol) and Lawesson's reagent (8.5 g, 21.0 mmol) were dissolved in anhydrous THF (55 mL) and the reaction was stirred for 3.5 hours at room temperature under nitrogen protection. The reaction was stirred at room temperature for 3.5 h under nitrogen protection. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Saturated aqueous NaHCO3 (100 mL) was added to the residue and stirring was continued for 1 hour. The aqueous phase suspension was extracted with EtOAc/CH2Cl2 (1:1, 400 mL), the organic phase was washed with saturated aqueous NaHCO3 solution (2 x 100 mL), and the combined aqueous phases were then extracted with EtOAc/CH2Cl2 (200 mL). All organic extracts were combined, dried with Na2SO4 and concentrated under reduced pressure to give tert-butyl (S)-2-thiocarbonylpyrrolidine-1-carboxylate as a white solid (8.74 g, 90% yield) with a melting point (EtOAc) of 190-192 °C. [α]D -103.4 (c 1.00, CHCl3). IR (KBr) 3380, 3202, 2981, 2881, 1671, 1411, 1166 cm-1. 1H NMR (400 MHz, CDCl3) δ= 1.41-1.50 (m, 9H), 1.65-2.75 (m, 4H), 3.22- 3.74 (m, 2H), 4.67 (dd, J = 8.0 and 3.6 Hz, 1H) ppm. HRMS (ESI) m/z calculated value C10H19N2O2S (M + H) 231.1162, measured value 231.1161.
References
[1] Journal of the American Chemical Society, 2002, vol. 124, # 6, p. 916 - 917
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2229 - 2233
[3] Tetrahedron Letters, 2011, vol. 52, # 42, p. 5435 - 5437
[4] Patent: US2011/65726, 2011, A1. Location in patent: Page/Page column 12
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 228 - 247
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Preparation Products And Raw materials
Raw materials
Preparation Products
(S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Suppliers
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- Product
- (S)-2-THIOCARBAMOYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 101410-18-8
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200kg
- Release date
- 2020-01-08