4-Nitrophenyl chloroformate → 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

HRID 1815571Notes

Reaction equation

HRID 1815571 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:14][C@@H:15]([OH:41])[C@@H:16]([NH:29][C:30](=[O:40])[O:31][C@@H:32]3[C@H:39]4[C@H:35]([O:36][CH2:37][CH2:38]4)[O:34][CH2:33]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl[C:47]([O:49][C:50]1[CH:55]=[CH:54][C:53]([N+:56]([O-:58])=[O:57])=[CH:52][CH:51]=1)=[O:48]>>[C:47](=[O:48])([O:49][C:50]1[CH:51]=[CH:52][C:53]([N+:56]([O-:58])=[O:57])=[CH:54][CH:55]=1)[O:28][CH2:27][CH2:26][CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][C@H:16]([NH:29][C:30]([O:31][C@@H:32]2[C@H:39]3[C@H:35]([O:36][CH2:37][CH2:38]3)[O:34][CH2:33]2)=[O:40])[C@H:15]([OH:41])[CH2:14][N:13]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])[CH2:42][CH:43]([CH3:45])[CH3:44])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 59997247(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-[4-(3-hydroxypropoxy)benzyl]propylcarbamate

Product 1

HCID 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

Procedure

(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-[4-(3-hydroxypropoxy)benzyl]propylcarbamate was treated with 4-nitrophenyl chloroformate as described previously to provide the title compound as a solid foam. 1H NMR (DMSO-d6): δ 0.86 (3H, d), 0.92 (3H, d), 1.2 (1H, dd), 1.38 (1H, quintuplet), 1.9-2.0 (1H, m), 2.05-2.15 (2H, m), 2.2 (1H, t), 2.6-2.8 (3H, m), 2.9 (1H, d), 2.96 (1H, dd), 3.2-3.3 (2H, m), 3.4-3.5 (1H, m), 3.5-3.6 (2H, m), 3.7 (1H, t), 3.8 (1H, dd), 4.0 (2H, t), 4.37 (2H, t), 4.8 (1H, dt), 5.0 (1H, d), 5.45 (1H, d), 6.18 (2H, s), 6.78 (2H, d), 7.0-7.1 (3H, m), 7.20-7.25 (2H, m), 7.3 (1H, dd), 7.56 (2H, d), 8.25 (2H, d); MS: 816 (MH+)

Sources & evidence

ORD record
ord-6c9e2fbfaced47f181a65e5573f804d7
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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