Phosphate → HCID 69663463, compound

HRID 1789624Notes

Reaction equation

O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:24][CH2:25][O:26][CH2:27][CH3:28])=[C:16]([CH:18]=[CH:19][C:20]([O:22]C)=[O:21])[CH:17]=1)=[O:10])([CH3:7])([CH3:6])[CH3:5].P([O-])([O-])([O-])=O>O1CCCC1.CO.O>[C:4]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:24][CH2:25][O:26][CH2:27][CH3:28])=[C:16]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])[CH:17]=1)=[O:10])([CH3:6])([CH3:7])[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

2.53 g (0.06 mol) of lithium hydroxide monohydrate was added at 0° C. to a solution of 6.3 g (0.018 mol) of methyl 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylate from step D in 50 mL of tetrahydrofuran, 15 mL of methanol and 30 mL of water. The mixture was allowed to agitate 24 hours at 60° C. The reaction mixture was then poured onto a phosphate buffer solution (pH 7.0) and extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous sodium chloride solution and then dried over sodium sulfate. The organic phase was partially evaporated to incipient formation of a precipitate, and hexane was then added. The precipitate was filtered off and washed with 50 mL of hexane. This gave 5.4 g (89% of the theoretical) of 3-(5-tert.butoxycarbonylamino-2-ethoxymethoxyphenyl)acrylic acid.

Workup

extractionextracted with ethyl acetate
washthe organic phase was washed with a saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
customThe organic phase was partially evaporated to incipient formation of a precipitate, and hexane
additionwas then added
filtrationThe precipitate was filtered off
washwashed with 50 mL of hexane

Sources & evidence

ORD record: ord-b8c3fe7d8c714fd3a9fe2ffe54494878
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07070626B2

Reaction notes

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