3-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid → HCID 71279106, compound

HRID 1621106Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[NH:17][C:18](=[NH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C.CCCCCCC>CN(C=O)C>[CH3:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:15])[CH2:10][C:11]1[O:13][N:25]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3-(tert-butoxycarbonylamino)-3-methylbutanoic acid (2.75 g, 12.7 mmol) and N,N′-carbonyldiimidazole (CDI; 2.05 g, 12.7 mmol) in DMF (20.0 mL) was stirred at RT under nitrogen atmosphere for 5 h. N-Hydroxybenzamidine (1.72 g, 12.7 mmol) was added and the reaction mixture was heated to 100° C. and stirred for 15 h. The crude reaction mixture was concentrated in vacuo, poured into ethyl acetate (100 mL) and extracted with water (3×100 mL). The combined aqueous layer was back-extracted with ethyl acetate (100 mL). The combined organic layer was dried over MgSO4, concentrated in vacuo and purified by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) to yield the product as white solid (2.72 g, 8.57 mmol, 67.5%). MS: M=318.1 (M+H)+

Workup

customThe crude reaction mixture
concentrationwas concentrated in vacuo
additionpoured into ethyl acetate (100 mL)
extractionextracted with water (3×100 mL)
extractionThe combined aqueous layer was back-extracted with ethyl acetate (100 mL)
dry with materialThe combined organic layer was dried over MgSO4
concentrationconcentrated in vacuo
custompurified by flash chromatography (

Sources & evidence

ORD record: ord-8698a80f0c8b4debbc08dada5b60f4e1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772510B2

Reaction notes

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