Sodium Hydroxide → HCID 19968861, compound
Reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][CH:12]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:13]([N:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])C)C1C=CC=CC=1.[OH-].[Na+]>C(O)C.C(O)(C)C.Cl.O.[Pd]>[CH3:1][NH:8][CH2:10][CH2:11][CH:12]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:13]([N:15]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14]Participants
8
Conditions
- Temperature
- 50 °C
Procedure
A solution of the product of step (a) (6.93 g, 19.0 mmol) in ethanol (60 ml) was added to a suspension of 10% Pd/C (10.67 g) in isopropanol (50 ml) plus 5 drops of concentrated hydrochloric acid. The reaction mixture was heated to 50° C. and 50 psi (about 3.5×105Nm-2) in a Parr bottle for 4 h. The catalyst was filtered off and the filtrate concentrated under reduced pressure to afford an oil. The oil was dissolved in water (80 ml), cooled (ice/water) and basified with aqueous sodium hydroxide (2M). The basic phase was washed with diethyl ether (3×50 ml) and the combined organic phases washed with brine (50 ml), water (50 ml), dried (MgSO4) and concentrated to afford the title compound as an oil (3.38 g, 68%).
Workup
- filtrationThe catalyst was filtered off
- concentrationthe filtrate concentrated under reduced pressure
- customto afford an oil
- washThe basic phase was washed with diethyl ether (3×50 ml)
- washthe combined organic phases washed with brine (50 ml), water (50 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-383079879317407a8e29d43506701667
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610295
Reaction notes
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