Hydrogen Bromide → HCID 131726855, compound
Reaction equation
[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:4](N[C@H](C(N1CCC[C@H]1C(O)=O)=O)C(C)C)=[O:5])[CH3:3].Cl.[NH2:32][C@H:33]([C:39]([N:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1)=[O:40])[CH2:34][CH2:35]C(=O)N.CN1CC[O:50][CH2:49][CH2:48]1.[N+](=[CH2:55])=[N-].[BrH:56]>C1COCC1.CCOCC>[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:4]([NH:32][C@H:33]([C:39]([N:41]1[CH2:42][CH2:43][CH2:44][C@H:45]1[C:49]([CH2:48][Br:56])=[O:50])=[O:40])[CH:34]([CH3:35])[CH3:55])=[O:5])[CH3:3]Participants
8
Conditions
- Temperature
- -15 °C
Procedure
4 (2.00 g, 4.76 mmol) was dissolved in 15 ml of dry THF and converted into a mixed anhydride (see compound 1) using CAIBE (0.623 ml, 4.76 mmol) and NMM (0.525 ml, 4.76 mmol). The precipitate formed was filtered off and cooled down to −15° C. Then diazomethane (23.8 mmol in 30 ml ether) was dropped into the solution under an argon atmosphere. After leaving the mixture for 1 h at 0° C. 1.27 ml of HBr (33% in AcOH) was added and the solution was stirred for 30 min at room temperature . . . . After that 70 ml of ether was added and the mixture was washed with 20 ml of water. The organic layer was separated and dried (Na2SO4) and evaporated.
Workup
- customThe precipitate formed
- filtrationwas filtered off
- customAfter leaving the mixture for 1 h at 0° C
- washthe mixture was washed with 20 ml of water
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-0c68ad533f4948ffb19d755dfa8158df
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368421B2
Reaction notes
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