Isopropyl chloroformate → HCID 44391407, compound

HRID 1243154Notes

Reaction equation

Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[CH2:8]([N:10]([CH2:31][CH3:32])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2([NH2:30])[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])=[CH:13][CH:12]=1)[CH3:9].C(N(CC)CC)C>O1CCCC1>[CH:5]([O:4][C:2](=[O:3])[NH:30][C:20]1([C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([N:10]([CH2:31][CH3:32])[CH2:8][CH3:9])=[CH:16][CH:15]=2)=[O:19])[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)([CH3:7])[CH3:6]

Participants

Conditions

Temperature: -40 °C

Procedure

The isopropyl chloroformate (18.4 mg, 0.15 mmol) was dissolved in anhydrous tetrahydrofuran (0.05 mL) and cooled at −40° C. A solution of amine from Example 8A (33.7 mg, 0.1 mmol) and triethylamine (0.021 mL, 0.15 mmol) in anhydrous tetrahydrofuran (0.5 mL) was added at −40° C. and reaction allowed to warm at room temperature, shaken overnight, then concentrated under reduced pressure. The residue was purified by reverse-phase HPLC to provide the title compound. Yield: 10.7 mg (25%). 1H NMR (500 MHz, DMSO-d6) δ 1.05 (m, 12H), 2.11 (m, 1H), 2.33 (d, J=17.15 Hz, 1H), 2.50 (m, 1H), 2.73 (m, 2H), 2.99 (d, J=16.53 Hz, 1H), 3.44 (m, 4H), 4.70 (m, 1H), 7.07 (m, 4H), 7.67 (d, J=15.0 Hz, 4H), 9.88 (s, 1H), 10.95 (s, 1H); MS (ESI): 424 (M+H)+, 422 (M−H)−.

Workup

customreaction
temperatureto warm at room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-9a96ca4375a04e05aeed10ade4616f0a
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115767B2

Reaction notes

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