4-Methyloxybenzyl chloride → 2-(S)-Hydroxy-3-(cyclopropyl)propanoic acid, 4-(methoxy)benzyl ester

HRID 1386696Notes

Reaction equation

HRID 1386696 reaction equation
[OH:1][C@@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>CN(C=O)C>[OH:1][C@@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([O:5][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)=[O:4]

Participants

4

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 21341065(S)-a-Hydroxy-cyclopropanepropanoic acid

Product 1

HCID 572090052-(S)-Hydroxy-3-(cyclopropyl)propanoic acid, 4-(methoxy)benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1.0 g (7.6 mmol) of 2-(S)-hydroxy-3-(cyclopropyl)propanoic acid (from EXAMPLE 21, Step A), 1.6 mL (11.4 mmol) of TEA and 1.6 mL (11.8 mmol) of 4-(methoxy)benzyl chloride in 10 mL of DMF using a procedure analogous to that described in EXAMPLE 20, Step G to provide 1.70 g (88%, ee=97.5%) of the title compound: RF: 0.20 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) 8-0.01-0.09 (m, 2H), 0.40-0.45 (m, 2H), 0.84 (m, 1H), 1.55-1.67 (m, 2H), 2.82 (br m, 1H), 3.81 (s, 3H), 4.25 (br m, 1H), 5.14 (ABq, J=11.8, 2H), 6.90 (d, J=8.7, 2H), 7.29 (d, J=8.7, 2H). HPLC Conditions:

Sources & evidence

ORD record
ord-78e02b0d5dd142e6829bfc492b986a38
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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