Sodium Carbonate → HCID 59568553, compound

HRID 216932Notes

Reaction equation

[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:30][O:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39]2[CH:40]=[C:41](B3OC(C)(C)C(C)(C)O3)[CH:42]=[CH:43][C:38]=2[O:37][C:36]1=[O:53].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:41]2[CH:42]=[CH:43][C:38]3[O:37][C:36](=[O:53])[N:35]([CH2:34][CH2:33][CH2:32][O:31][CH3:30])[C:39]=3[CH:40]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 363 mg) and 3-(3-methoxypropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2(3H)-one (Example 11, step (ii), 234 mg) in acetonitrile (8 mL) were treated with aqueous sodium carbonate (2M, 0.70 mL) and nitrogen was bubbled through the mixture. 1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added and the mixture was heated at 85° C. for 18 h. The mixture was purified by chromatography on silica eluting with 50-100% ethyl acetate/isohexane to yield the sub-titled compound (151 mg).

Workup

customwas bubbled through the mixture
addition1,1 bis(Di-tert-butylphosphino)ferrocene palladium dichloride (5 mg) was added
customThe mixture was purified by chromatography on silica eluting with 50-100% ethyl acetate/isohexane

Sources & evidence

ORD record: ord-c80ba5e71fa44deb9c8b767818e2b8b1
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193239B2

Reaction notes

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