Diisopropylamine → HCID 86749013, compound

HRID 2209434Notes

Reaction equation

[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]1([CH2:19][CH2:20][C:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH2:32][C:33]([O:35]C)=[O:34].[Cl-].[NH4+]>O1CCCC1>[C:13]1([CH2:19][C:20]([CH2:32][C:33]([OH:35])=[O:34])([CH3:1])[C:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve diisopropylamine (0.88 mL, 6.28 mmol) in tetrahydrofuran (7.5 mL). Cool in an ice bath and add, by dropwise addition, n-butyllithium (3.6 mL of a 1.6M solution in hexanes, 5.75 mmol). Stir for 15 minutes, then cool to -78° C. Add a solution of 3 -phenylpropionic acid, t-butyldimethylsilyl ester (1.33 g, 5.04 mmol) in tetrahydrofuran (5 mL). Stir for 45 minutes then add methyl bromoacetate (949 mg, 6.2 mmol). Stir for 3 hours, add saturated ammonium chloride (6 mL) and warm to room temperature. Partition between ethyl ether (75 mL) and water (10 mL). Dry (Na2SO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give 3-phenyl-2-methylcarboxymethylpropionic acid, t-butyldimethylsilyl ester.

Workup

temperatureCool in an ice bath
stirringStir for 45 minutes
stirringStir for 3 hours
temperaturewarm to room temperature
customPartition between ethyl ether (75 mL) and water (10 mL)
dry with materialDry (Na2SO4)
customevaporate the solvent in vacuo
custompurify by silica gel chromatography

Sources & evidence

ORD record: ord-cb13b4d6ae1948b5a30ea8c04ab21708
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455242

Reaction notes

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