Tetrahydrofuran → (+/-)-tert-Butyl 1-(3-{[cyclopentyl(4-vinylphenyl)acetyl]amino}benzyl)cyclopropanecarboxylate

HRID 1475656Notes

Reaction equation

[H-].[Na+].[CH:3]1([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH2:37]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]1([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=[CH2:37])=[CH:31][CH:30]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:26]=[CH:27][CH:28]=2)[CH2:15][C:16]2([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:18][CH2:17]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

39.0 mg (0.98 mmol, 60% in mineral oil) of sodium hydride were suspended in 3.0 ml of abs. THF, the mixture was cooled to 0° C. and 301.8 mg (0.84 mmol) of methyltriphenylphosphonium bromide were added. The mixture was stirred at 0° C. for 30 min, and 300 mg (0.65 mmol) of (+/−)-tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]amino}benzyl)cyclopropanecarboxylate were then added. The reaction mixture was stirred at RT overnight and then concentrated under reduced pressure. The residue was taken up in acetonitrile and filtered, and the filtrate obtained was purified by preparative RP-HPLC (mobile phase acetonitrile/water). This gave 219.3 mg (73.4% of theory) of the target compound.

Workup

stirringThe reaction mixture was stirred at RT overnight
concentrationconcentrated under reduced pressure
filtrationfiltered
customthe filtrate obtained
customwas purified by preparative RP-HPLC (mobile phase acetonitrile/water)

Sources & evidence

ORD record: ord-38c69bb09cc1405bad17f99eaad2dd80
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018258B2

Reaction notes

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