Ethyl bromoacetate → HCID 136386266, compound

HRID 535262Notes

Reaction equation

[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:16])[C:10]2[NH:11][CH:12]=[N:13][C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[C:1]([NH:6][C:7]1[NH:8][C:9](=[O:16])[C:10]2[N:11]=[CH:12][N:13]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:14]=2[N:15]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 10 (2.21 g, 10 mmol) and Na2CO3 (2.12 g, 20 mmol) were suspended in dry DMF, and the mixture was warmed to 80° C. with stirring. After 1 h the heating was terminated, and the reaction mixture was cooled to 0° C. and ethyl bromoacetate (1.22 mL, 11 mmol) was added dropwise for 1 h. The stirring was continued for an additional 2 h. The reaction mixture was filtered and the solid was washed with DCM. The filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography ((DCM/MeOH; 9.5/0.5) to obtain 11 as a white solid: yield 0.77 g (25%); MS(+ESI): m/z 308 [M+H]+; 1H NMR (400 MHz, CDCl3): δ11.99 (s, 1H), 8.50 (s, 1H), 7.71 (s, 1H), 4.80 (s, 2H), 4.26 (q, 2H, J=6.8 Hz), 2.70 (septet, 1H, J=6.8 Hz), 1.31 (t, 3H, J=6.8 Hz), 1.28 (d, 6H, J=6.8 Hz); 13C NMR (400 MHz, CDCl3): δ178.3, 166.9, 155.4, 148.5, 147.6, 139.2, 120.8, 62.3, 44.5, 36.5, 18.9, 14.1.

Workup

customAfter 1 h the heating was terminated
temperaturethe reaction mixture was cooled to 0° C.
filtrationThe reaction mixture was filtered
washthe solid was washed with DCM
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2189547288164e74ac1ef14889d8be85
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859490B2

Reaction notes

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