Water → HCID 15294452, compound
Reaction equation
[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([OH:28])[CH3:27])[C:4](=O)[CH2:5][CH2:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].O>C1COCC1>[CH2:1]([N:3]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([OH:28])[CH3:27])[CH2:4][CH2:5][CH2:6][CH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:10][CH:9]=1)[OH:19])[CH3:2]Participants
Procedure
A solution of the product from Step IV (1.34 g, 3.28 mmol) in THF (25 ml) was added during 45 minutes under nitrogen, to an ice cold, stirred suspension of LiAlH4 (0.31 g, 8.2 mmol) in THF (10 ml). The mixture was kept in the ice bath for 90 minutes and then treated cautiously with a solution of saturated aqueous sodium potassium tartrate (6.5 ml) and water (6.5 ml). The mixture was stirred for 90 minutes in the ice bath and then extracted with EtOAc. The extract was washed with brine, dried (MgSO4) and concentrated; the residue was chromatographed over silica gel with 1% NH4OH-10% MeOH--CHCl3 to give 0.72 g of the titled product which is a compound of Formula I'. The high resolution FAB mass spectrum had (M+H)+ at m/z 401. Theory for C20H37N2O4S: 401.24; measured: 401.2480.
Workup
- extractionextracted with EtOAc
- washThe extract was washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customthe residue was chromatographed over silica gel with 1% NH4OH-10% MeOH
Sources & evidence
- ORD record
- ord-d11e24496c064b0980e06db2fb92bcce
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05405997
Reaction notes
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