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Cas Database

101715-65-5

101715-65-5

Identification

Synonyms:[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester

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Relevant articles and documentsAll total 2 Articles be found

Facile ring opening reaction of oxazolone enables efficient amidation for aminoisobutyric acid

Jo, Minmi,Won, Sun-Woo,Lee, Dong Guk,Yun, Jungeon,Kim, Sunhong,Kwak, Young-Shin

, p. 481 - 489 (2018/05/03)

Abstract: 4,4-Dimethyloxazolones derived from N-protected aminoisobutyric acid (AIB) are particularly known as poor electrophiles due to the steric hindrance around the carbonyl and not employed as useful intermediates for amidation whereas numerous examp

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Valeur, Eric,Bradley, Mark

, p. 8855 - 8871 (2008/02/11)

Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%.

Process route upstream and downstream products

Process route

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

2-(benzyloxy)-4,4-dimethyloxazol-5(4H)-one
367274-58-6

2-(benzyloxy)-4,4-dimethyloxazol-5(4H)-one

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester
101715-65-5

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester

Conditions
Conditions Yield
In toluene; at 70 ℃; for 3h; Reagent/catalyst; Temperature;
92%
Z-Aib-OH
15030-72-5

Z-Aib-OH

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester
101715-65-5

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester

2-(benzyloxy)-4,4-dimethyloxazol-5(4H)-one
367274-58-6

2-(benzyloxy)-4,4-dimethyloxazol-5(4H)-one

Conditions
Conditions Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20 - 80 ℃;
10%
80%
Z-Aib-OH
15030-72-5

Z-Aib-OH

cyclohexylamine
108-91-8,157973-60-9

cyclohexylamine

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester
101715-65-5

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester

Conditions
Conditions Yield
With PS-N-isobutoxycarbonyl-2-isobutoxy-1,2-dihydroquinoline; In acetonitrile; at 20 ℃; for 24h;
61%
Z-Aib-OH
15030-72-5

Z-Aib-OH

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester
101715-65-5

[1-(cyclohexylmethyl-carbamoyl)-1-methylethyl]carbamic acid benzyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / -72 °C
2: toluene / 3 h / 70 °C
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; toluene;
Multi-step reaction with 2 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 20 - 80 °C
2: toluene / 3 h / 70 °C
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In toluene;

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