Ammonium Hydroxide → HCID 59997321, compound

HRID 1815573Notes

Reaction equation

HRID 1815573 reaction equation
[C:1](=[O:57])(OC1C=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.[OH-].[NH4+:59]>>[NH2:59][C:1]([O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C@H:14]([NH:35][C:36](=[O:37])[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)[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:23])=[O:24])[CH2:18][CH:19]([CH3:20])[CH3:21])=[CH:11][CH:12]=1)=[O:57]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 599973373-(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

Product 1

HCID 59997321HCID 59997321, compound

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 concentrated ammonium hydroxide as described above to afford the title compound as a white solid. 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.82 (3H, d), 1.2-1.3 (1H, m), 1.4 (1H, quintuplet), 1.9-2.0 (3H, m), 2.2 (1H, t), 2.6-2.8 (3H, m), 2.9 (1H, d), 2.97 (1H, dd), 3.2-3.3 (1H, m), 3.4-3.6 (4H, m), 3.7 (1H, t), 3.8 (1H, dd), 3.9 (2H, t), 4.0 (2H, t), 4.8 (1H, dt), 5.0 (1H, d), 5.5 (1H, d), 6.17 (2H, s), 6.4 (2H, br s), 6.78 (2H, d), 7.0-7.1 (3H, m), 7.2-7.3 (3H, m); MS: 694 (MH+)

Sources & evidence

ORD record
ord-58e61e75d2be40d3896b85b88a47754a
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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