HCID 86622989, compound → HCID 86622990, compound

HRID 2233801Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:23][C:24]1[CH:33]=[CH:32][C:27]2[O:28]C(=O)[O:30][C:26]=2[CH:25]=1)[C:10]([O:12][C@H:13]([CH3:22])[C@H:14]([O:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH3:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(=O)(O)[O-].[Na+].C(#N)C>[OH:30][C:26]1[CH:25]=[C:24]([CH2:23][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][C@H:13]([CH3:22])[C@H:14]([O:16][C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH3:15])=[O:11])[CH:33]=[CH:32][C:27]=1[OH:28]

Participants

Conditions

Temperature: 60 °C

Procedure

(1R,2R)-1-Methyl-2-(2-methylpropanoyloxy)propyl (2S)-2-[(tert-butoxy)carbonylamino]-3-(2-oxobenzo[3,4-d]1,3-dioxolen-5-yl)propanoate (17) (6.4 g, 13.83 mmol) was dissolved in 50 mL of mixture of sat. sodium bicarbonate and acetonitrile (1:1). The resulting mixture was stirred at 60° C. under nitrogen for 60 min. TLC indicated a completed reaction. Acetonitrile was removed under reduced pressure. The product was extracted with methyl tert-butyl ether. The organic layer was collected, washed with 10% citric acid, dried over MgSO4, and concentrated to provide the title compound (18) (6.7 g, 100% yield). 1H NMR (400 MHz, CDCl3): δ 1.13-1.16 (m, 12H), 1.42 (s, 9H), 2.54 (m, 1H, J=7.2 Hz), 2.94 (d, 2H, J=6.0 Hz), 4.47 (dd, 1H, J=6.8, 14 Hz), 4.91 (m, 1H), 4.97 (m, 1H), 5.02 (d, 1H, NH, J=8.4 Hz), 6.53 (dd, 1H, J=2, 8 Hz), 6.66 (d, 1H, J=2 Hz), 6.74 (d, 1H, J=8 Hz). MS (ESI) m/z 439.9 (M+H)+.

Workup

customa completed reaction
customAcetonitrile was removed under reduced pressure
extractionThe product was extracted with methyl tert-butyl ether
customThe organic layer was collected
washwashed with 10% citric acid
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-8d08d1ff75484f90b28aae83e2b97109
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709527B2

Reaction notes

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