(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

Base Information

Chemical Name:(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester
CAS No.:127152-90-3
Molecular Formula:C₂₄H₂₇F₂NO₅
Molecular Weight:447.479
Hs Code.:

Synonyms:(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

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Chemical Property of (+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

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Technology Process of (+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

There total 5 articles about (+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

: 108-24-7
acetic anhydride

: 127152-83-4
(+/-)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>-α-aminobenzenepropanoic acid phenylmethyl ester p-toluenesulfonate

: 127152-90-3
(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

Guidance literature:: With triethylamine; In dichloromethane; for 2h;
DOI:10.1021/jm00107a037

Reference yield:

: 5524-56-1
ethyl 2-p-tolyl-2-oxoacetate

: 127152-90-3
(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / (dimethylamido)sulfur trifluoride (DAST) / 0 - 20 °C

2: 84 percent / 5 N aq. KOH / acetonitrile / 1 h / Ambient temperature

3: oxalyl chloride, DMF / toluene / 20 h / Ambient temperature

4: DMF / toluene / 24 h / Ambient temperature

5: 73 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / Heating

6: 1.) lithium diisopropylamide / 1.) THF, HMPA, -78 deg C, 15 min, 2.) from -78 deg C to RT, 2 h

7: 70 percent / acetonitrile; H₂O / 2 h / Ambient temperature

8: 63 percent / Et₃N / CH₂Cl₂ / 2 h

With potassium hydroxide; N-Bromosuccinimide; Perbenzoic acid; oxalyl dichloride; (dimethylamido)sulfur trifluoride; triethylamine; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrachloromethane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jm00107a037

Reference yield:

: 131323-06-3
α,α-difluoro-4-methylbenzeneacetic acid ethyl ester

: 127152-90-3
(+/-)-α-(acetylamino)-4-<1,1-difluoro-2-(1,1-dimethylethoxy)-2-oxoethyl>benzenepropanoic acid phenylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / 5 N aq. KOH / acetonitrile / 1 h / Ambient temperature

2: oxalyl chloride, DMF / toluene / 20 h / Ambient temperature

3: DMF / toluene / 24 h / Ambient temperature

4: 73 percent / N-bromosuccinimide (NBS), benzoyl peroxide / CCl₄ / Heating

5: 1.) lithium diisopropylamide / 1.) THF, HMPA, -78 deg C, 15 min, 2.) from -78 deg C to RT, 2 h

6: 70 percent / acetonitrile; H₂O / 2 h / Ambient temperature

7: 63 percent / Et₃N / CH₂Cl₂ / 2 h

With potassium hydroxide; N-Bromosuccinimide; Perbenzoic acid; oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrachloromethane; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jm00107a037