tert-butyl N-(3-bromopropyl)carbamate → 3-(3-tert-Butoxycarbonylaminopropoxy)-5-(4-cyanophenoxy)benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2].[C:22]([O:26][C:27](=[O:33])[NH:28][CH2:29][CH2:30][CH2:31]Br)([CH3:25])([CH3:24])[CH3:23]>>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:8]=[C:9]([O:11][CH2:31][CH2:30][CH2:29][NH:28][C:27]([O:26][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:33])[CH:10]=1)[CH3:2]Participants
3
Procedure
Following the procedure of Example 69(b) 3-(4-cyano-phenoxy)-5-hydroxy-benzoic acid ethyl ester 0.9 g (3.17 mmol) and (3-bromo-propyl)-carbamic acid tert-butyl ester (1.5 g, 6.34 mmol) were used to afford 0.95 g of the required product. 1H NMR (DMSO-d6): δ 2.05 (4H, m), 3.35 (2H, m), 3.90 (3H, s), 4.08 (211, t), 4.72 (1H, brs), 6.78 (1H, t), 7.02 (2H, d), 7.28 (1H, s), 7.41 (1H, s), 7.62 (2H, d), 8.05 (1H, brs).
Sources & evidence
- ORD record
- ord-b480aa103b9b4dcdb6f5f8c550a56ff1
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722930B2
Reaction notes
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