5-chloro-6-[(triisopropylsilyl)oxy]-1,3-benzoxazol-2(3H)-one → N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide

HRID 270131Notes

Reaction equation

Br[Mg][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:8][C:9]1[C:10]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[CH:11][C:12]2[O:16][C:15](=[O:17])[NH:14][C:13]=2[CH:18]=1>O1CCCC1>[Cl:8][C:9]1[C:10]([O:19][Si:20]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:21]([CH3:22])[CH3:23])=[CH:11][C:12]([OH:16])=[C:13]([NH:14][C:15]([CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[O:17])[CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Bromo(cyclopentyl)magnesium (0.58 mL, 1.16 mmol, 2 M in diethylether) was added under inert atmosphere to a solution of 5-chloro-6-[(triisopropylsilyl)oxy]-1,3-benzoxazol-2(3H)-one (66 mg, 0.19 mmol) in tetrahydrofuran (3 mL). After stirring over night at 70° C., the solution was evaporated and dissolved in ethylacetate. The organic layer was washed with water and 1M hydrochloric acid, dried and finally concentrated to give 68 mg (89%) of the subtitled compound as a brown solid.

Workup

customthe solution was evaporated
dissolutiondissolved in ethylacetate
washThe organic layer was washed with water and 1M hydrochloric acid
customdried
concentrationfinally concentrated

Sources & evidence

ORD record: ord-79fd2906d9eb4002a0171c82a134f06d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449475B2

Reaction notes

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