3-Pyridinemethanol → HCID 70060615, compound
Reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:16][C:17](=[O:33])[CH:18]([NH:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41]O)[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:34])[CH:7]([NH:16][C:17](=[O:33])[CH:18]([NH:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:41][C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]Participants
6
Procedure
A solution of the product from Example 24 (0.3 g, 0.63 mmol), 3-pyridylmethanol (0.061 mL, 0.63 mmol) and triphenylphosphine (0.165 g, 0.63 mmol) in 10 mL of tetrahydrofuran at 0° C. was treated with diethylazodicarboxylate (0.11 g, 0.63 mmol). The reaction mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was concentrated, and the residue was taken up in EtOAc and washed with sat. aqueous NaHCO3 and brine. The organic phase was dried with Na2SO4, filtered, and concentrated. The residue was purified by HPLC to give the title compound (0.047 g).
Workup
- concentrationThe reaction mixture was concentrated
- washwashed with sat. aqueous NaHCO3 and brine
- dry with materialThe organic phase was dried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-ade2fc9e260d4b2e9a2cac789d5878d1
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06423689B1
Reaction notes
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