Cesium carbonate → 4-(4-Carbamoyl-3-cyclohexylmethoxy-phenoxy)-butyric Acid Ethyl Ester

HRID 1018670Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]([OH:18])[CH:10]=1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]([O:18][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To 4-(4-carbamoyl-3-hydroxy-phenoxy)-butyric acid ethyl ester (3.0 g, 11.22 mmol) in DMF (25 mL) was added Cs2CO3 (5.11 g, 15.71 mmol) followed by (bromomethyl)cyclohexane (1.72 mL, 12.34 mmol). The mixture was heated to 60° C. for 6 h, then dumped onto ice/H2O. The formed solids were collected by filtration (H2O wash)and dried in vacuuo (3.74 g, 92%). MS [M+H]+ 364. m.p. 98-99° C.

Workup

filtrationThe formed solids were collected by filtration (H2O
customwash)and dried in vacuuo (3.74 g, 92%)

Sources & evidence

ORD record: ord-27cb1a66840d4e8d8f4ce0f6e0dd53a0
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482852B2

Reaction notes

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