Dimethylformamide → 3-[2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

HRID 1181128Notes

Reaction equation

[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33][OH:34])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[H-].[Na+]>CCOC(C)=O>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:11][C:10]=1[CH2:33][O:34][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -10 °C

Procedure

A 100 mL round bottomed flask was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-hydroxymethylphenyl]propionic acid tert-butyl ester (1.52 g, 3.10 mmol), anhydrous DMF (15 mL), and then benzyl bromide (1.84 mL, 15.5 mmol) under a nitrogen atmosphere. The solution was cooled to −10° C., and NaH (0.124 g, 3.10 mmol, 60% oil dispersion) was added. The mixture was stirred for 5 h, and was poured into EtOAc (150 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a brown oil. The crude oil was purified using radial chromatography (EtOAc:hexanes 2:98 to 5:95) to give a pale yellow oil (1.04 g, 58%). MS (ES) m/e 598 (M+NH4).

Workup

washThe organic layer was washed with brine (2×)
dry with materialdried (Na2SO4)
concentrationconcentrated to a brown oil
customThe crude oil was purified

Sources & evidence

ORD record: ord-e965ca0df51a495c9f0228ea867c9b3d
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

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