HCID 59997325, compound → HCID 59997352, compound

HRID 1815568Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:14][C@@H:15]([OH:42])[C@@H:16]([NH:30][C:31](=[O:41])[O:32][C@@H:33]3[C@H:40]4[C@H:36]([O:37][CH2:38][CH2:39]4)[O:35][CH2:34]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:47][N:48]=[C:49]=[O:50].ClCCl>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:43][CH:44]([CH3:46])[CH3:45])[CH2:14][C@@H:15]([OH:42])[C@@H:16]([NH:30][C:31](=[O:41])[O:32][C@@H:33]3[C@H:40]4[C@H:36]([O:37][CH2:38][CH2:39]4)[O:35][CH2:34]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:49]([NH:48][CH3:47])=[O:50])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Reactant 2

HCID 59997325HCID 59997325, compound

HCID 86593034HCID 86593034, compound

Product 1

HCID 59997352HCID 59997352, compound

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-(4-hydroxybutoxy)benzyl]propylcarbamate was treated with methyl isocyanate/dichloromethane as described earlier to afford the title compound as a solid foam. 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.82 (3H, d), 1.2 (1H, dd), 1.4 (1H, quintuplet), 1.6-1.8 (4H, m), 1.9-2.0 (1H, m), 2.38 (1H, t), 2.5 (3H, d), 2.7-2.8 (3H, m), 2.9 (1H, d), 2.98 (1H, dd), 3.3-3.4 (1H, m), 3.4-3.5 (1H, m), 3.5-3.6 (3H, m), 3.7 (1H, t), 3.8 (1H, dd), 3.9 (2H, t), 3.95 (2H, t), 4.8 (1H, dt), 5.0 (1H, br s), 5.5 (1H, d), 6.18 (2H, s), 6.78 (2H, d), 6.9 (1H, br s), 7.0-7.1 (3H, m), 7.2 (1H, d), 7.25 (1H, s), 7.3 (1H, d); MS: 744 (M+23); C34H47N3O12S.

Sources & evidence

ORD record: ord-07b0f4cd9b4048d9bccbb8ed533e0aaf
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878728B1

Reaction notes

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