Sodium hydride → HCID 90037018, compound

HRID 1055361Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][OH:16])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].F[C:18]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]>CN(C=O)C>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:18]=1[O:16][CH2:15][C@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[C:12]([OH:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of NaH (60% in mineral oil, 1.48 g, 36.9 mmol, Eq: 2.10) inDMF (15 mL) was cooled to 0° C. and (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (3.61 g, 17.6 mmol, Eq: 1.00) in DMF (15 mL) was added dropwise over 15 min. The mixture was stirred at 0° C. for 30 min. and at room temp. (RT) for 30 min. The mixture was cooled to 0° C. and methyl 2-fluoro-3-nitrobenzoate (3.5 g, 17.6 mmol, Eq: 1.00) in DMF (15 mL) was added dropwise over 10 min. After 2.5 h the mixture was diluted with ice cold H2O and extracted with EtOAc. The combined extracts were dried over Na2SO4 filtered and concentrated to give a residue that was purified by chromatography to afford 2-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-3-nitrobenzoic acid methyl ester (4.3 g, 50%) as a yellow foam.

Workup

temperatureThe mixture was cooled to 0° C.
additionAfter 2.5 h the mixture was diluted with ice cold H2O
extractionextracted with EtOAc
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a residue that
customwas purified by chromatography

Sources & evidence

ORD record: ord-f085f2a5bb994d858ecfdee17cdc233a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394263B2

Reaction notes

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