Water → HCID 58391157, compound
Reaction equation
[N:1]([C@@H:4]([C@@H:28]([CH3:31])[CH2:29][CH3:30])[C:5]([N:7]([C@@H:12]([CH:25]([CH3:27])[CH3:26])[CH2:13][C@H:14]([C:16]1(C(NC)=O)[NH:20][CH:19]=[CH:18][S:17]1)[OH:15])[CH2:8][CH2:9][O:10][CH3:11])=[O:6])=[N+:2]=[N-:3].C(O[C:36](=[O:38])[CH3:37])(=O)C.[N:39]1[CH:44]=CC=C[CH:40]=1.[OH2:45]>ClCCl.CN(C1C=CN=CC=1)C>[C:36]([O:15][C@@H:14]([C:16]1[S:17][CH:18]=[C:19]([C:40](=[O:45])[NH:39][CH3:44])[N:20]=1)[CH2:13][C@@H:12]([N:7]([CH2:8][CH2:9][O:10][CH3:11])[C:5](=[O:6])[C@@H:4]([N:1]=[N+:2]=[N-:3])[C@@H:28]([CH3:31])[CH2:29][CH3:30])[CH:25]([CH3:27])[CH3:26])(=[O:38])[CH3:37]Participants
Procedure
To a solution of the compound obtained in example 15.1 (0.2 mmole, 90 mg) in dichloromethane (8 mL), kept under stirring, were added acetic anhydride (1 mmole, 94 μL), pyridine (0.5 mmole, 40 μL) and a catalytic amount of DMAP. Stirring was continued for 3 hours. At the end the reaction mixture was diluted with H2O (10 mL) and extracted with dichloromethane (2×5 mL). The organic phases were pooled and washed, in the order, with a NaHCO3 saturated aqueous solution (1×10 mL), with a 1N aqueous solution of HCl (1×10 mL) and with brine (1×10 mL). The organic phase were dried over Na2SO4, filtered and concentrated under vacuum to give 92 mg (93% yield) of (1R,3R)-3-((2S,3S)-2-azido-N-(2-methoxyethyl)-3-methylpentanamido)−4−methyl-1-(4-(methylcarbamoyl)thiazol-2-yl)pentyl acetate. Rf=0.32 (petroleum ether/ethyl acetate 1/1 volume/volume).
Workup
- stirringStirring
- extractionextracted with dichloromethane (2×5 mL)
- washwashed, in the order, with a NaHCO3 saturated aqueous solution (1×10 mL), with a 1N aqueous solution of HCl (1×10 mL) and with brine (1×10 mL)
- dry with materialThe organic phase were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-89d3675bd18449fd89190b98bbca2880
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580820B2
Reaction notes
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