Hydrochloric Acid → ((3-(Trifluoromethyl)benzoyl)amino)acetic acid

HRID 1809861Notes

Reaction equation

[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12].Cl>CC#N.[OH-].[Na+]>[F:6][C:7]([F:17])([F:18])[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a rapid stirring solution of glycine (15.014 g, 0.20 mol) in MeCN (400 mL) and 2 M NaOH (250 mL) at 0° C. was slowly added a solution of 3-(trifluoromethyl)-benzoyl chloride (41.714 g, 0.20 mol) in 75 mL of MeCN over 30 min. The cloudy yellow solution was stirred at 0° C. for 30 min. The reaction mixture was acidified with 3 M HCl to pH=3, followed by removal of MeCN on rotary evaporator. The resulting mixture was then extracted with EtOAc (400 mL×3). The combined organic layers were dried, filtered and concentrated to give a light yellow solid (48.53 g), which was triturated with toluene (500 mL). After filtration, the solid product was washed with cold toluene until the filtrate was colorless. After dried under high vacuum over the weekend, a white powder product: 44.60 g (90%) was afforded. MS (M+H+)=248.1. 1H NMR (DMSO-d6) δ 12.70 (br s, 1H), 9.17 (m, 1H), 8.20 (dd, 2H), 7.94 (dd, 1H), 7.78 (m, 1H), 3.97 (d, 2H).

Workup

customfollowed by removal of MeCN on rotary evaporator
extractionThe resulting mixture was then extracted with EtOAc (400 mL×3)
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-05abfac33ffa44948550b09d30c157fd
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362003B2

Reaction notes

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