Allyl bromide → HCID 57814144, compound

HRID 564395Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][N:5]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:4][C@@H:3]1[NH:13][C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1.[H-].[Na+].[CH2:32](Br)[CH:33]=[CH2:34]>CN(C=O)C>[CH2:34]([O:1][C@H:2]1[CH2:6][N:5]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH2:4][C@@H:3]1[NH:13][C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=1)[CH:33]=[CH2:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(2-((3S,4S)-4-hydroxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-ylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (50 mg, 0.1 mmol) in DMF (1 mL), was added NaH (17 mg, 0.4 mmol) at 0° C. The mixture was stirred at 0° C. for 10 min., followed by addition of allyl bromide (0.011 mL, 0.13 mmol). The mixture was stirred at 0° C. for 30 min., and the organic phase was washed with water, dried over MgSO4, concentrated, and subjected to flash chromatography (EtOAc:MeOH:Et3N 9:1:0.1) to generate the title compound (6 mg, 10% yield). 1H-NMR (CDCl3) δ: 1.40-1.57 (m, 2H), 1.70-1.90 (m, 2H), 2.27-2.40 (m, 2H), 2.70-2.82 (m, 2H), 3.30-3.42 (m, 3H), 3.77-3.85 (m, 1H), 3.90-4.05 (m, 3H), 4.06-4.22 (m, 3H), 4.29-4.32 (m, 1H), 5.10-5.30 (m, 2H), 5.80-5.98 (m, 1H), 6.60 (d, J=8.1 Hz, 1H), 7.10 (s, 1H), 7.57 (t, J=8.1 Hz, 1H), 7.77 (d, J=7.2 Hz, 1H), 8.00 (d, J=5.4 Hz, 1H), 8.08 (s, 1H). MS m/z: 456 (M+1)

Workup

stirringThe mixture was stirred at 0° C. for 30 min.
washthe organic phase was washed with water
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-688ac549ec6144f2a88ef241b5e72041
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067457B2

Reaction notes

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