Benzyl Alcohol → HCID 118363874, compound
Reaction equation
CC[N:3]([CH:7](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.[C:27]([O:31][C:32]([N:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[C@H:39]([C:43]1[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[C:45]([F:53])[CH:44]=1)C(O)=O)=[O:33])([CH3:30])([CH3:29])[CH3:28].[CH2:54]([OH:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C1(C)C=CC=CC=1>[CH2:54]([O:61][C:7]([NH:3][C@@H:39]([C:43]1[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[C:45]([F:53])[CH:44]=1)[C@@H:35]1[CH2:36][CH2:37][CH2:38][N:34]1[C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])=[O:17])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of DIPEA (0.598 mL, 3.43 mmol), diphenylphosphoryl azide (0.591 mL, 2.74 mmol) and toluene (15 mL) was added 57 (0.895 g, 2.29 mmol). After agitating for 30 min, the mixture was heated to 100° C. and agitated for 3 h. The mixture was then cooled to 70° C., and benzyl alcohol (2 mL, 18.5 mmol) was added and the mixture stirred overnight. After evaporating to dryness, the crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 20% EtOAc) to afford 1.04 g (88%) of 61 as a solid.
Workup
- stirringagitated for 3 h
- temperatureThe mixture was then cooled to 70° C.
- stirringthe mixture stirred overnight
- customAfter evaporating to dryness
- customthe crude product was purified by SiO2 chromatography
- washeluting with an EtOAc/hexane gradient (10 to 20% EtOAc)
Sources & evidence
- ORD record
- ord-66e133865faf427fa33f7ac10a919909
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187462B2
Reaction notes
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