4-(Benzyloxy)benzene-1-sulfonyl chloride → methyl (1S,2R)-2-({[4-(benzyloxy)phenyl]sulfonyl}amino)-1-methylcyclopentanecarboxylate
Reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([CH3:11])[C:7]([O:9][CH3:10])=[O:8].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C@@H:2]2[CH2:6][CH2:5][CH2:4][C@:3]2([CH3:11])[C:7]([O:9][CH3:10])=[O:8])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
3
Procedure
According to the procedure of Example 47, Step 4, using methyl (1S,2R)-2-amino-1-methylcyclopentanecarboxylate (480 mg, 2.48 mmol) and 4-(benzyloxy)benzene-1-sulfonyl chloride (0.692 g, 2.45 mmol), methyl (1S,2R)-2-({[4-(benzyloxy)phenyl]sulfonyl}amino)-1-methylcyclopentanecarboxylate was obtained (811 mg, 82%) as a colorless solid after purification via column chromatography on silica gel eluting with 25% ethyl acetate/hexane. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.20 (s, 3H) 1.45-1.56 (m, 3H) 1.68-1.77 (m, 1H) 2.10 (ddd, J=12.57, 8.53, 3.66 Hz, 1H) 3.27-3.36 (m, 1H) 3.64-3.67 (m, 3H) 5.10 (s, 2H) 5.61 (d, J=10.11 Hz, 1H) 7.00-7.05 (m, 2H) 7.31-7.43 (m, 5H) 7.78-7.83 (m, 2H).
Sources & evidence
- ORD record
- ord-975e32bbd75f497c89e83acfed3a6f4c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595327B2
Reaction notes
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