Triethylamine → HCID 86587276, compound

HRID 392813

Reaction equation

HRID 392813 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(O)(=O)[C@H](CC(O)=O)O.C(N(CC)CC)C.[C:29]([Si:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:32])([CH3:31])[CH3:30]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([O:10][Si:33]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:9])[C:4](=[O:11])[O:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 222656L-Malic AcidHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 86587276HCID 86587276, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-(+)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid (2.08 g, 11.9 mmol), which was derived from L-malic acid by means known in the art, in dry dichloromethane (20 ml) was treated with triethylamine (1.83 ml, 13.1 mmol) followed by a solution of t-butylchlorodiphenylsilane (3.44 g, 12.5 mmol) in dichloromethane (5 ml) added dropwise over 5 minutes. After 3 hours at 22° C., the reaction mixture was diluted with toluene (250 ml) washed with water, saturated sodium bicarbonate, brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm) using a mixture of toluene and ethyl acetate (0-2%) as eluent gave 4.90 g (99%) of the title material as a clear oil. 1H NMR (400 MHz, CDCl3) δ: 1.13 (s, 9), 1.58 (s, 3), 3.05 (m, 2), 4.79 (dd, 1, J=4, 7), 7.4-7.8 (m, 10).

Workup

  1. additionadded dropwise over 5 minutes
  2. washwashed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure and chromatography of the residue on silica gel (4×12 cm)
  5. additiona mixture of toluene and ethyl acetate (0-2%) as eluent

Sources & evidence

ORD record
ord-cbfcffe2f321494b9f6b949aed7e6a8e
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Linked notes

Loading…