75885-58-4

Basic information

• Product Name: (S)-(+)-2,2-Dimethylcyclopropanecarboxamide
• Synonyms: (S)-2,2-DIMETHYL-CYCLOPROPANECARBOXYLIC ACID AMIDE;S-(+)-2,2-DIMETHYLCYCLOPROPANE-1-CARBOXAMIDE;(S) 2,2-DIMETHYL CYCLOPROPANE CARBOXAMIDE;(S)-(+)-2,2-DIMETHYLCYCLOPROPANECARBOXAMIDE;(1S)-2,2-DIMETHYLCYCLO-PROPANECARBOXAMIDE;CYCLOPROPANECARBOXAMIDE, 2,2-DIMETHYL-, (1S)-;(S)-(+)-DMCPA;(S)(R)-(+)-2,2-Dimethyl Cycolpropane Carboxamide
• CAS NO: 75885-58-4
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• EINECS: 278-334-3
• Product Categories: AMIDE;Amides;Chiral Compounds;chiral;API intermediates;API;Amides (Chiral);Chiral Building Blocks;Cyclopropanes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound;Chiral Building Blocks;Organic Building Blocks
• Mol File: 75885-58-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 135-137 °C(lit.)
• Boiling Point: 203 - 204
• Flash Point: 89.933 °C
• Appearance: White to Off-white/Crystalline Powder
• Density: 1g/cm
• Vapor Pressure: 0.088mmHg at 25°C
• Refractive Index: 83 ° (C=1, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in methanol
• PKA: 16.61±0.40(Predicted)
• CAS DataBase Reference: (S)-(+)-2,2-Dimethylcyclopropanecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2,2-Dimethylcyclopropanecarboxamide(75885-58-4)
• EPA Substance Registry System: (S)-(+)-2,2-Dimethylcyclopropanecarboxamide(75885-58-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 75885-58-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Employed in the preparation of (Z)-2-(acylamino)-3-substituted propenoic acids as inhibitors of the mammalian β-lactamase renal dipeptidase.

InChI:InChI=1/C6H11NO/c1-6(2)3-4(6)5(7)8/h4H,3H2,1-2H3,(H2,7,8)/t4-/m1/s1

Synthetic route

(+)-1S-2,2-dimethylcyclopropane-carboxylic acid (14590-53-5) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
Stage #1: (+)-1S-2,2-dimethylcyclopropane-carboxylic acid With thionyl chloride In dichloromethane at 20℃; Stage #2: With ammonia In dichloromethane at -15℃;	92.1%
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 1.5 h / Ambient temperature 2: 83 percent / 3 M NH3 / ethanol / 0.75 h View Scheme

(S)-ethyl 2,2-dimethylcyclopropanecarboxylate (89007-61-4) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With thionyl chloride; ammonia In dichloromethane	90.7%
With ammonia; calcium chloride In methanol at 100 - 110℃;	10 g

(+)-N-<<(2,2-dimethylcyclopropyl)carbonyl>oxy>succinimide (107871-21-6) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonium hydroxide In ethanol for 0.75h;	83%

2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanone (220263-88-7) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With aminolysis	72%

(RS)-2,2-dimethylcyclopropanecarboxamide (1759-55-3) → (R)-2,2-dimethylcyclopropanecarboxylic acid (28624-52-4) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With water In acetonitrile at 30℃; for 2.33333h; pH=8.2; Solvent; Concentration; Enzymatic reaction; enantioselective reaction;	A n/a B 43.5%
With R-amidase from Delftia tsuruhatensis CCTC M 205114 at 35℃; for 18h; Large scale reaction; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	A n/a B 34.2%

2,2-dimethylcyclopropane carboxylic acid 2,2,2-trifluoroethyl ester (645413-67-8) → C8H11F3O2 + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30 - 40℃; for 20h; Product distribution / selectivity; Enzymatic reaction;	A n/a B 40%

(R)-2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanol (220263-87-6) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Na2Cr2O7, H2SO4 / acetic acid 2: 72 percent / aminolysis View Scheme

2,2-dimethylcyclopropane-1-carboxylic acid (75885-59-5) → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
Multi-step reaction with 3 steps 2: 93 percent / pyridine / 1.5 h / Ambient temperature 3: 83 percent / 3 M NH3 / ethanol / 0.75 h View Scheme

C9H16O3 → C9H16O3 + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30℃; for 20h; Product distribution / selectivity; Enzymatic reaction;	A n/a B n/a

C8H13BrO2 → C8H13BrO2 + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30℃; for 20h; Product distribution / selectivity; Enzymatic reaction;	A n/a B n/a

C8H13ClO2 → C8H13ClO2 + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; Candida antarctica Type B lipase In tert-butyl alcohol at 30℃; for 20h; Product distribution / selectivity; Enzymatic reaction;	A n/a B n/a

ethyl (E)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate (1022895-93-7) → ethyl-7-Chloro-2-oxoheptanoate (78834-75-0) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
Stage #1: ethyl (E)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate With toluene-4-sulfonic acid In dichloromethane at 20℃; Stage #2: With sodium hydroxide; water In dichloromethane pH=8 - 9; Product distribution / selectivity;
Stage #1: ethyl (E)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate With methanesulfonic acid In toluene at 30℃; Stage #2: With sodium hydroxide; water In toluene pH=8 - 9; Product distribution / selectivity;

(S)-isopropyl 2,2-dimethylcyclopropanecarboxylate → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; calcium chloride In methanol at 100 - 110℃;	10 g

(S)-methyl 2,2-dimethylcyclopropanecarboxylate → (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4)

Conditions	Yield
With ammonia; calcium chloride In methanol at 100 - 110℃; Solvent; Reagent/catalyst; Temperature;	9 g

ethyl-7-Chloro-2-oxoheptanoate (78834-75-0) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (Z)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid ethyl ester (877758-94-6)

Conditions	Yield
Stage #1: ethyl-7-Chloro-2-oxoheptanoate; (S)-2,2-dimethylcyclopropanecarboxamide With toluene-4-sulfonic acid In toluene for 10h; Reflux; Stage #2: at 30℃; for 1h; Solvent; Temperature; Irradiation;	99.5%

5,10,15,20-tetrakis(3-bromophenyl)porphyrin + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → C68H66N8O4

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h; Inert atmosphere; Schlenk technique;	97%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(3,5-dimethoxyphenyl)porphyrin → C72H74N8O8

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 48h;	88%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis[4-(tert-butyl)phenyl]porphyrin → C76H82N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 40h;	86%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + β-bromo-5,10,15,20-tetraphenylporphyrin → (S)-(+)-2,2-dimethylcyclopropanecarboxylic acid (5,10,15,20-tetraphenylporphyrin-2-yl)amide

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate In tetrahydrofuran at 100℃; for 24h;	86%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis[3,5-di(tert-butyl)phenyl]porphyrin → C84H98N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 48h;	85%
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate In tetrahydrofuran at 100℃; for 48h;	85%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene Inert atmosphere;	85%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 72h; Schlenk technique; Inert atmosphere; Sealed tube;

5,15-bis(2,6-dibromophenyl)-10,20-bis[3,5-di(tert-butyl)phenyl]porphyrin + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → C20H8N4H2(C6H3(C(CH3)3)2)2(C6H3(NHCOC3H3(CH3)2)2)2

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Schlenk technique; Inert atmosphere; Sealed tube; Molecular sieve;	85%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(2,4,6-trimethylphenyl)porphyrin → C74H78N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 56h;	84%

5,15-bis(2,6-dibromophenyl)-10,20-bis(3,5-di(2,4,6-trimethylphenyl)phenyl)porphyrin + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → C104H106N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 72h; Inert atmosphere;	82%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 72h; Inert atmosphere; Schlenk technique;	82%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)porphyrin → C56H58N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	79%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-diphenylporphyrin → C68H66N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	78%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(4-trifluoromethylphenyl)porphyrin → C70H64F6N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	77%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bisheptylporphyrin → C70H86N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	74%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(4-acetylphenyl)porphyrin → C72H70N8O6

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	66%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(2,6-dimethoxyphenyl)-porphyrin → C72H74N8O8

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	59%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 72h; Schlenk technique; Inert atmosphere; Sealed tube;

5,15-bis(2,6-dibromophenyl)-10,20-bis(2,6-dimethoxyphenyl)porphyrin + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → C20H8N4H2(C6H3(OCH3)2)2(C6H3(NHCOC3H3(CH3)2)2)2

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Schlenk technique; Inert atmosphere; Sealed tube; Molecular sieve;	59%

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) + 5,15-bis(2,6-dibromophenyl)-10,20-bis(2,3,4,5,6-pentafluorophenyl)porphyrin → C68H56F10N8O4

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; for 60h;	46%

8-bromo-2-oxooctanoic acid + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (Z)-8-Bromo-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-oct-2-enoic acid (107912-87-8)

Conditions	Yield
In toluene Heating;	44%

C40H28Br4N4O3 + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → C52H48Br2N6O5 + C64H68N8O7

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 125℃; for 65h; Inert atmosphere;	A 21% B 41%

2-oxooctanoic acid (328-51-8) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (+)-(Z)-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid

Conditions	Yield
In toluene for 17h; Heating;	31%

7-bromo-2-oxoheptanoic acid (107872-93-5) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (Z)-7-bromo-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid (78834-80-7)

Conditions	Yield
In toluene Heating;	28%

2-Oxobutyric acid (600-18-0) + (S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (Z)-2-[((S)-2,2-Dimethyl-cyclopropanecarbonyl)-amino]-but-2-enoic acid

Conditions	Yield
In toluene Heating;

(S)-2,2-dimethylcyclopropanecarboxamide (75885-58-4) → (+)-1S-2,2-dimethylcyclopropane-carboxylic acid (14590-53-5)

Conditions	Yield
hydrolysis;

Upstream product

• 220263-88-7 2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanone 
• 1759-55-3 (RS)-2,2-dimethylcyclopropanecarboxamide 
• 89007-61-4 (S)-ethyl 2,2-dimethylcyclopropanecarboxylate 
• 1022895-93-7 ethyl (E)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoate 
• 645413-67-8 2,2-dimethylcyclopropane carboxylic acid 2,2,2-trifluoroethyl ester 
• 14590-53-5 (+)-1S-2,2-dimethylcyclopropane-carboxylic acid 
• 75885-59-5 2,2-dimethylcyclopropane-1-carboxylic acid 
• 220263-87-6 (R)-2,2,2-Trichloro-1-((S)-2,2-dimethyl-cyclopropyl)-ethanol 
• 107871-21-6 (+)-N-<<(2,2-dimethylcyclopropyl)carbonyl>oxy>succinimide 

Downstream Products

• 877674-77-6 (Z)-7-chloro-2 ((2s)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid 
• 166037-21-4 7-chloro-2-[[(1S)-2,2-dimethylcyclopropane]carboxamide]-2-heptenoic acid 
• 166037-21-4 (E)-7-chloro-2[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid 
• 82009-34-5 cilastatine 
• 14590-53-5 (+)-1S-2,2-dimethylcyclopropane-carboxylic acid 
• 85394-14-5 (+)-(Z)-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid 

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R-Stereoselective amidase, a key enzyme responsible for the formation of chiral center of cilastatin, has been cloned from Delftia tsuruhatensis and expressed in Escherichia coli under T7 promoter. This recombinant amidase exhibits strict R-selectivity towards 2,2-dimethylcyclopropanecarboxamide (DMCPCA). The amidase activity of the engineered E. coli strain reached 2963 U/L in a 5-L bioreactor, which was 8.27 times higher than that of D. tsuruhatensis, and was further increased to 5255 U/L in a 100-L bioreactor. Using cell-free extract prepared from 1 kg (wet cell weight) of recombinant E. coli cells as catalyst, 60 kg of R,S-DMCPCA was resolved into S-DMCPCA (28.6 kg) and R-2,2-dimethylcyclopropanecarboxylic acid (R-DMCPCS 31.7 kg) in 18 h, and the enantiomeric excess (ee) value of S-DMCPCA reached 99.32%. During the purification process, 24.6 kg of S-DMCPCA was eluted from adsorption resin HZ801 with 80% (v/v) acetone, and then 20.5 kg of pure S-DMCPCA was obtained after concentration and crystallization, corresponding to a total yield of 34.2% from R,S-DMCPCA. Therefore, the industrial production process of S-DMCPCA was successfully established using recombinant R-amidase from D. tsuruhatensis.