Sodium Bicarbonate → HCID 69763206, compound

HRID 1006100Notes

Reaction equation

[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8](=[O:27])[C@H:9]([NH:12][S:13]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[C:18](C)[C:17]=3[CH3:26])(=[O:15])=[O:14])[CH2:10][OH:11])=[CH:4][C:3]=2[O:2]1.O.[C:33]1(C)C=[CH:37][C:36](S(O)(=O)=O)=[CH:35][CH:34]=1.C(=O)(O)[O-:45].[Na+]>C(Cl)Cl.O1C=CCCC1>[CH2:1]1[O:31][C:30]2[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8](=[O:27])[C@H:9]([NH:12][S:13]([C:16]3[C:17]([CH3:26])=[CH:18][C:19]([O:23][CH3:24])=[CH:20][C:21]=3[CH3:22])(=[O:15])=[O:14])[CH2:10][O:11][CH:37]3[CH2:36][CH2:35][CH2:34][CH2:33][O:45]3)=[CH:4][C:3]=2[O:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

2(R)-(4-methoxy-2,3,6-trimethylbenzenesulfonylamino)-3-hydroxypropionic acid 3,4-methylenedioxybenzyl ester (38.4 g) was dissolved in methylene chloride (140 mL) and dihydropyran (23 mL). The reaction mixture was cooled to 0° C. and p-toluenesulfonic acid monohydrate (0.78 g) was added. After 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate (200 mL). The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo. This residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes) to afford 2(R)-(4-methoxy-2,6-dimethylbenzenesulfonyl-amino)-3-(tetrahydropyran-2-yloxy)propionic acid 3,4-methylenedioxybenzyl ester (41.4 g).

Workup

customThe organic layer was separated
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThis residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-a1f89f9d6e3347acb7a0f6d1f8ca21ed
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787559B2

Reaction notes

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