Triethylamine → HCID 123623320, compound

HRID 1523284Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][C:39]([F:42])([F:41])[F:40])=[CH:34][CH:33]=1)=[O:31]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([CH2:17][C:18]([O:20][CH2:29][C:30](=[O:31])[C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]([F:40])([F:41])[F:42])=[CH:34][CH:33]=2)=[O:19])[CH2:16][CH2:15][O:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(3-{[(Benzyloxy)carbonyl]amino}tetrahydrofuran-3-yl)acetic acid (Preparation 24, 0.311 g, 1.11 mmol) and triethylamine (0.233 mL, 1.67 mmol) were stirred in acetone (4 mL). A solution of 2-bromo-1-[4-(trifluoromethoxy)phenyl]ethanone (0.315 g, 1.11 mmol) in acetone (4 mL) was added and the reaction heated to 50° C. for 1 hour. Rapid formation of a white precipitate was observed. The reaction was partitioned between dichloromethane and water. The organic layer was separated by phase separation cartridge and concentrated in vacuo to afford the title compound as an oil which was used without purification in the next step (0.634 g, 118% yield).

Workup

customThe reaction was partitioned between dichloromethane and water
customThe organic layer was separated by phase separation cartridge
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7f603036ec2c404e86c94002a5a1a57b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079878B2

Reaction notes

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