Sodium Sulfite → HCID 58456373, compound
Reaction equation
[OH:1][C@:2]1([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.C1C(=O)N([Br:28])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[Br:28][C:18]1[S:17][C:16]([C@@:2]2([OH:1])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:4][CH2:3]2)=[N:20][CH:19]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
The product of Step 2 (14.5 g, 48.6 mmol) was dissolved in DMF (58 mL) and then treated with NBS (11.24 g, 63.2 mmol) and warmed to 40° C. for 3 hours. The reaction was quenched with Na2SO3 (3.0 g, 24.30 mmol) in H2O (50 mL) and the solution was then extracted with EtOAc (100 mL), washed with brine (50 mL) and then chromatographed on silica gel to afford tert-butyl (4R)-4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxyazepane-1-carboxylate (18.3 g, 46 mmol). MS ESI: [M+H-tBu]+ m/z 320.
Workup
- extractionthe solution was then extracted with EtOAc (100 mL)
- washwashed with brine (50 mL)
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-0fdef05ede12409285b0ce6f9abb5b15
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
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