tert-Butanol → Tert-butyl 2-methylbenzo[d]oxazol-6-ylcarbamate

HRID 340438Notes

Reaction equation

C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])=CC=1.C[C:31]1[O:32][C:33]2C=C(C(O)=O)[CH:37]=[CH:36][C:34]=2[N:35]=1>O1CCOCC1>[C:8]([O:12][C:31](=[O:32])[NH:35][C:34]1[CH:33]=[CH:7][C:6]2[N:3]=[C:4]([CH3:5])[O:20][C:37]=2[CH:36]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Triethylamine (765 μl), tert-butylalcohol (10 ml), and DPPA (1.18 ml) were added to a 1,4-dioxane (20 ml) solution containing 2-methyl-1,3-benzoxazol-6-carboxylic acid (885 mg), followed by stirring at 100° C. for 1 hour and 30 minutes. The solvent was distilled away under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography, and a white solid of tert-butyl(2-methyl-1,3-benzoxazol-6-yl)carbamate (1.00 g) was thus obtained.

Workup

distillationThe solvent was distilled away under reduced pressure
additiona saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added
customThe organic layer was collected
washwashed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled away under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-77d309918e6a4ca1b40e99974ae27f6c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895585B2

Reaction notes

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