Dimethylformamide → Benzyl (2R)-2-Benzyl-3-chloromethylcarbonylpropionate

HRID 973500Notes

Reaction equation

[C:1]([CH2:4][C@@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([OH:3])=O.C(Cl)(=O)[C:24]([Cl:26])=O.CN(C)C=O.Cl.O1CCOCC1>C(Cl)Cl>[CH2:16]([C@H:5]([CH2:4][C:1]([CH2:24][Cl:26])=[O:3])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The resultant acid from Example 23 (500 mg, 1.68 mmol) in CH2Cl2 (8 ml) at 0° C. was treated with oxalyl chloride (0.160 ml, 1.83 mmol) and dimethylformamide (0.0065 ml). After 2 h at 0° C., the solvent was evaporated and the residue was dissolved in ether (6 ml), cooled to 0° C. and treated with an ether solution of CH2N2. After 2 h at 0° C. the solvent was evaporated and the residue was dissolved in ether (6 ml), cooled to -10° C., and treated with 4.0M HCl/ dioxane (0.6 ml, 2.4 mmol). After 1 h the solvent was evaporated and the residue was chromatographed on silica gel with 10% ethyl acetate in hexane to afford 476.8 mg (83%) of a colorless oil. 1H NMR (CDCl3) δ7.08-7.40 (m,10H), 5.12 (d,1H), 5.08 (d,1H), 4.02 (s,2H), 3.30 (m,1H), 3.10 (dd,1H), 2.97 (dd,1H), 2.78 (dd,1H), 2.55 (dd,1H).

Workup

customthe solvent was evaporated
dissolutionthe residue was dissolved in ether (6 ml)
additiontreated with an ether solution of CH2N2
customAfter 2 h at 0° C. the solvent was evaporated
dissolutionthe residue was dissolved in ether (6 ml)
temperaturecooled to -10° C.
customAfter 1 h the solvent was evaporated
customthe residue was chromatographed on silica gel with 10% ethyl acetate in hexane

Sources & evidence

ORD record: ord-4be3c1d78adf459fb4ddd6c8936bf91d
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05063208

Reaction notes

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