Acetic Acid → HCID 68748209, compound

HRID 1183153Notes

Reaction equation

[NH2:1][C:2]1([CH2:5][O:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:24]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)[C:25]([C:27]5([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]5)=[O:26])=[CH:20][C:19]=4[F:40])=[CH:12][CH:13]=[N:14]3)=[CH:9][C:8]=2[O:41][CH3:42])[CH2:4][CH2:3]1.[O:43]1[CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]1.CC(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:40][C:19]1[CH:20]=[C:21]([N:24]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[C:25]([C:27]2([C:30]([NH2:32])=[O:31])[CH2:29][CH2:28]2)=[O:26])[CH:22]=[CH:23][C:18]=1[O:17][C:11]1[C:10]2[C:15](=[CH:16][C:7]([O:6][CH2:5][C:2]3([NH:1][CH:46]4[CH2:47][CH2:48][O:43][CH2:44][CH2:45]4)[CH2:3][CH2:4]3)=[C:8]([O:41][CH3:42])[CH:9]=2)[N:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 30 °C

Procedure

The product of Example 2 (200 mg) was mixed with tetrahydro-4H-pyran-4-one (45 mg), NaHB(OAc)3 (96 mg) and HOAc (42 mg) in DCM (5 ml). The reaction mixture was stirred at 30° C. overnight. Saturated NaHCO3 (20 ml) was added to the reaction and the solution was further extracted with EtOAc twice. The combined organic layer was washed with water, brine and dried over Na2SO4. The solution was evaporated and purified by preparative TLC plate to give the titled compound. Mass: (M+1), 659

Workup

extractionthe solution was further extracted with EtOAc twice
washThe combined organic layer was washed with water, brine
dry with materialdried over Na2SO4
customThe solution was evaporated
custompurified by preparative TLC plate

Sources & evidence

ORD record: ord-80319c85d6e5437b92353a925f09e747
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664244B2

Reaction notes

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