9H-Purine-9-acetic acid, 6-[[(phenylmethoxy)carbonyl]amino]- → 4-{[6-N-(Benzyloxycarbonyl)-adenin-9-yl]acetyl}-(2-nitro-benzenesulfonyl)-piperazin-2-one
Reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C:15]1=[O:20])(=[O:13])=[O:12])([O-:4])=[O:3].[CH2:21]([O:28][C:29]([NH:31][C:32]1[N:40]=[CH:39][N:38]=[C:37]2[C:33]=1[N:34]=[CH:35][N:36]2[CH2:41][C:42](O)=[O:43])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([O:28][C:29]([NH:31][C:32]1[N:40]=[CH:39][N:38]=[C:37]2[C:33]=1[N:34]=[CH:35][N:36]2[CH2:41][C:42]([N:17]1[CH2:18][CH2:19][N:14]([S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N+:2]([O-:4])=[O:3])(=[O:12])=[O:13])[C:15](=[O:20])[CH2:16]1)=[O:43])=[O:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1Participants
3
Procedure
The title compound (731 mg, 61%) was synthesized by reaction of 1-(2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (644 mg, 2.0 mmol) with [6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid (655 mg, 2.0 mmol) as per the procedure of example 77. 1H NMR (DMSO-d6) δ 10.69 (s, 1H), 9.00 (m, 1H), 8.71 (m, 1H), 8.63˜8.58 (m, 2H), 8.31 (s, 0.6H), 8.29 (s, 0.4H), 7.47˜7.33 (m, 5H), 5.39 (s, 1.2H), 5.29 (s, 0.8H), 5.21 (s, 2H), 4.57 (s, 0.8H), 4.29 (s, 1.2H), 4.15˜4.09 (m, 2.4H), 3.93˜3.86 (m, 1.6H).
Sources & evidence
- ORD record
- ord-77c2581082384ec6acafb266507a176d
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022851B2
Reaction notes
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