Dichloromethane → HCID 21196095, compound

HRID 1066817Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[F:22][C:23]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:24]=1[CH2:25]Br.C(Cl)Cl>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][O:13][CH2:25][C:24]1[CH:27]=[C:28]([Br:31])[CH:29]=[CH:30][C:23]=1[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -45 °C

Procedure

A stirred solution of 4-(t-butoxycarbonylamino)-3,3-dimethylbutan-1-ol (1.0 g, 4.60 mmol) in tetrahydrofuran (33 ml) at −45° C. was treated with potassium t-butoxide (1 M in tetrahydrofuran, 5.06 ml, 5.06 mmol). The anion was stirred for 30 minutes at −45° C., then cooled to −78° C. and treated with a tetrahydrofuran solution of 2-fluoro-5-bromobenzyl bromide (1.23 g, 4.60 mmol). The resulting yellow mixture was slowly warmed to 0° C. and stirred for about four hours. The cloudy reaction mixture was diluted wtih methylene chloride (100 ml) and washed with 1 M potassium carbonate. The organic fraction was dried over sodium sulfate, filtered, and the solvents were removed in vacuo. The residue was further purified by preparative high performance liquid chromatography to yield 1.38 grams (74%) of the title intermediate as a colorless oil.

Workup

temperaturecooled to −78° C.
temperatureThe resulting yellow mixture was slowly warmed to 0° C.
stirringstirred for about four hours
customThe cloudy reaction mixture
washwashed with 1 M potassium carbonate
dry with materialThe organic fraction was dried over sodium sulfate
filtrationfiltered
customthe solvents were removed in vacuo
customThe residue was further purified by preparative high performance liquid chromatography

Sources & evidence

ORD record: ord-263070a68c5046078afcb7451df50e5a
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245761B1

Reaction notes

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