Ammonium Chloride → HCID 59355151, compound
Reaction equation
Br[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][CH2:8][CH2:9][C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)[C:3]=1[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=1.[Li]C(C)(C)C.[NH4+].[Cl-]>C1COCC1>[OH:30][CH:24]([C:21]1[CH:22]=[CH:23][C:18]([C:3]2[C@@H:4]([CH2:7][CH2:8][CH2:9][C:10]3[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=3)[CH2:5][CH2:6][CH:2]=2)=[CH:19][CH:20]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
A −78° C. solution of 9 (10 mg, 0.02 mmol) in THF (0.4 mL) was treated with tert-BuLi (60 μL, 0.01 mmol, 1.7 M/pentane). After 30 min., 2 mL saturated NH4Cl solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. The crude product still contained vinyl bromide 9 and so was resubmitted to the reaction conditions: THF (0.2 mL) and tert-BuLi (100 mL,) were added and the reaction was stirred for 3 h at −40° C. and then worked up as above. Purification by flash chromatography on silica gel (0%→30% MeOH/CH2Cl2) gave compound 11 (4 mg, 0.01 mmol, 50%).
Workup
- extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
- dry with materialThe combined dichloromethane solution was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe crude product still contained vinyl bromide 9 and so was resubmitted to the reaction conditions
- customPurification by flash chromatography on silica gel (0%→30% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-f23989bb8f4049f3b6c58b1ca46be32d
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713968B2
Reaction notes
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