Dimethylformamide → HCID 10938596, compound

HRID 724780Notes

Reaction equation

[CH2:1]([O:8][CH:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[F:32][C:33]([F:42])([F:41])[C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37]>ClCCl.CN(C)C1C=CN=CC=1.O>[CH2:14]([O:13][CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:10]([NH:37][C:36]1[CH:38]=[CH:39][CH:40]=[C:34]([C:33]([F:32])([F:41])[F:42])[CH:35]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of dibenzyloxyacetic acid (4.0 g) in dichloromethane (40 ml) was cooled to 0° C. and treated dropwise with, successively, DMF (100 mg) and oxalyl chloride (2.0 g). After 30 min pyrridine (3.52 g), 3-trifluoromethyl aniline (2.64 g) and 4-dimethylaminopyridine (100 mg) were added. The mixture was stirred at 0° C. for a further 30 min then allowed to warm to room temperature. After 3 hours the mixture was poured into water, extracted with ethyl acetate and the extracts washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate solution and brine. After drying (MgSO4) the extracts were evaporated under reduced pressure to give the sub-title compound (5.62 g) as an orange gum, sufficiently pure to be used in step d).

Workup

temperatureto warm to room temperature
extractionextracted with ethyl acetate
washthe extracts washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate solution and brine
dry with materialAfter drying (MgSO4) the extracts
customwere evaporated under reduced pressure

Sources & evidence

ORD record: ord-17c135ac41b2489c95fa9f435492cdd8
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705456

Reaction notes

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