3-(4-{(2S,3R)-2-({[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-4-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-3-hydroxybutyl}phenoxy)propyl 4-nitrophenyl carbonate → HCID 59997187, compound
Reaction equation
[C:1](=O)([O:47]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:35][C:36]([O:38][C@@H:39]2[C@H:46]3[C@H:42]([O:43][CH2:44][CH2:45]3)[O:41][CH2:40]2)=[O:37])[C@H:15]([OH:34])[CH2:16][N:17]([S:22]([C:25]2[CH:33]=[CH:32][C:28]3[O:29][CH2:30][O:31][C:27]=3[CH:26]=2)(=[O:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:9][CH:8]=1.[CH3:58][NH2:59].O1CCCC1>>[O:29]1[C:28]2[CH:32]=[CH:33][C:25]([S:22]([N:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[CH2:16][C@@H:15]([OH:34])[C@@H:14]([NH:35][C:36](=[O:37])[O:38][C@@H:39]3[C@H:46]4[C@H:42]([O:43][CH2:44][CH2:45]4)[O:41][CH2:40]3)[CH2:13][C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][C:1]([NH:59][CH3:58])=[O:47])=[CH:12][CH:11]=3)(=[O:24])=[O:23])=[CH:26][C:27]=2[O:31][CH2:30]1Participants
3
Procedure
3-(4-{(2S,3R)-2-({[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-4-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-3-hydroxybutyl}phenoxy)propyl 4-nitrophenyl carbonate was treated with 2M methylamine/tetrahydrofuran as described above to provide the title compound as a white solid. 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.84 (3H, d), 1.1-1.2 (1H, m), 1.2 (1H, br quintuplet), 1.9-2.0 (3H, m), 2.17 (1H, t), 2.45 (3H, d), 2.6-2.8 (3H, m), 2.83-3.00 (2H, m), 3.4-3.6 (5H, m), 3.7 (1H, br s), 3.8 (1H, br s), 3.9 (2H, br s), 4.0 (2H, br s), 4.8-4.9 (1H, m), 5.0 (1H, d), 5.5 (1H, d), 6.17 (2H, s), 6.7-6.8 (2H, m), 6.9 (1H, br s), 7.0-7.1 (3H, m), 7.2-7.4 (3H, m); MS: 708 (MH+);
Sources & evidence
- ORD record
- ord-5efa5a79e1fd40d4a6ee6f88270f4784
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06878728B1
Reaction notes
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