Sodium Carbonate → HCID 69199501, compound

HRID 2377656Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH:10]([CH2:19][CH2:20][CH:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[OH:22])[C:9]2=[O:30])=[CH:4][CH:3]=1.[C:31]([O:35][C:36](=[O:39])[CH2:37]Br)([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH2:37][C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:39])=[CH:16][CH:17]=3)[CH:10]([CH2:19][CH2:20][CH:21]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[OH:22])[C:9]2=[O:30])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl) azetidin-2-one (J. Med. Chem. 1998, 41, 973-980; 50 mg, 0.122 mmol), tert-butylbromoacetate (24 μl, 0.165 mmol), sodium carbonate (80 mg, 0.76 mmol) and a catalytic amount of caesium carbonate were added to MeCN (3 ml) and the mixture was stirred for 1.5 hours at 50° C. The solids were filtered off and the solvent was evaporated under reduced pressure. Purification of the residue by column chromatography using DCM/EtOAc (100/7) as eluent gave 35 mg, (55%) of the title compound. NMR (300 MHz): 1.45 (s, 9H), 1.8-2.1 (m, 4H), 2.25-2.3 (m, 1H), 3.05-3.15 (m, 1H), 4.5 (s, 2H), 4.55-4.6 (m, 1H), 4.75 (bs, 1H), 6.9-7.3 (m, 12H); m/z 524.3.

Workup

filtrationThe solids were filtered off
customthe solvent was evaporated under reduced pressure
customPurification of the residue by column chromatography

Sources & evidence

ORD record: ord-e5e3f62c74094e82b4f61a0e696d0d40
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470678B2

Reaction notes

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