tert-Butyl bromoacetate → HCID 131714543, compound

HRID 482920Notes

Reaction equation

[O-:1][C:2]#[N:3].[K+].Br[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:14]([O:18][C:19]([NH:21][C@H:22]1[C@H:25]([CH3:26])[NH:24][C:23]1=[O:27])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([O:18][C:19]([NH:21][C@H:22]1[C@H:25]([CH3:26])[N:24]([C:2]([NH:3][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:1])[C:23]1=[O:27])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of potassium cyanate (186 mg, 2.3 mmol) in 2 ml of dimethylformamide was added t-butyl bromoacetate (0.356 ml, 2.2 mmol). The mixture was heated to 100° C. for 1 hour and cooled to room temperature. (3S-trans)-3-[[(t-Butyloxy)carbonyl]amino]-4-methyl-2-azetidinone (400 mg, 2.0 mmol) was then added, and the mixture was heated to 140° C. for 1 hour. Upon cooling to room temperature, the crude product was extracted from ice cold 5% HCl with three portions of ethyl acetate. The combined organic layers were extracted twice with water, once with aqueous potassium bicarbonate, and dried over sodium sulfate. The volatiles were removed, and the residue was subjected to chromatography on silica gel (eluting with 40% ethyl acetate-hexane) yielding 149 mg of the title compound.

Workup

temperaturecooled to room temperature
temperaturethe mixture was heated to 140° C. for 1 hour
temperatureUpon cooling to room temperature
extractionthe crude product was extracted from ice cold 5% HCl with three portions of ethyl acetate
extractionThe combined organic layers were extracted twice with water, once with aqueous potassium bicarbonate
dry with materialdried over sodium sulfate
customThe volatiles were removed

Sources & evidence

ORD record: ord-cea0261d1bdc41cb871b20f45ec77301
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04576749

Reaction notes

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