HCID 69906549, compound → HCID 76106777, compound

HRID 1107172Notes

Reaction equation

HRID 1107172 reaction equation
[OH:1][NH:2]C(=O)C(CCOC1C=CC=CC=1)C(S(C1C=CC(OC)=CC=1)(=O)=O)CCCCC1C=CC=CC=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45]([CH:48]([CH2:62][CH2:63][CH2:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[CH:49]([CH2:53][CH2:54][S:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[C:50]([OH:52])=[O:51])(=[O:47])=[O:46])=[CH:41][CH:40]=1>>[OH:1][NH:2][C:50](=[O:51])[C@@H:49]([CH2:53][CH2:54][S:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C@H:48]([S:45]([C:42]1[CH:43]=[CH:44][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)(=[O:47])=[O:46])[CH2:62][CH2:63][CH2:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1.[CH3:37][O:38][C:39]1[CH:40]=[CH:41][C:42]([S:45]([CH:48]([CH2:62][CH2:63][CH2:64][CH2:65][C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=2)[CH:49]([CH2:53][CH2:54][S:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[C:50]([OH:52])=[O:51])(=[O:47])=[O:46])=[CH:43][CH:44]=1.[OH:1][NH:2][C:50](=[O:51])[CH:49]([CH2:53][CH2:54][S:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[CH:48]([S:45]([C:42]1[CH:43]=[CH:44][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)(=[O:47])=[O:46])[CH2:62][CH2:63][CH2:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

5

Reactant 2

HCID 69906549HCID 69906549, compoundHCID 76125203HCID 76125203, compound

Product 3

HCID 54144645HCID 54144645, compoundHCID 69906549HCID 69906549, compoundHCID 76106777HCID 76106777, compoundYield 79%

Procedure

The titled compound is prepared according to the method used in the preparation of (±)-(2R*, R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenoxyethyl)heptanoic acid hydroxyamide, except using (±)-(2R*, 3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenylsulfanyl-ethyl)heptanoic acid as the starting material. From (±)-(2R*, 3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenylsulfanylethyl)heptanoic acid (0.64 g, 1.2 mmol) provides (±)-(2R*, 3R*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(2-phenylsulfanylethyl)heptanoic acid hydroxyamide (0.5 g, 79%): 1H NMR (300 MHz, CDCl3) δ 9.44 (bs, 1H), 7.75 (d, J=8.9 Hz, 2H), 7.28-7.14 (m, 8H), 7.05 (d, J=7.2 Hz, 2H), 6.99 (d, J=9.0 Hz, 2H), 3.88 (s, 3H), 3.28-3.25 (m, 1H), 3.00-2.93 (m, 2H), 2.75-2.66 (m, 1H), 2.46 (t, J=7.3 Hz, 2H), 2.43-2.30 (m, 1H) 1.83-1.17 (m, 8H); MS (FAB) m/e 528 (M+H)+ ; Anal. (C28H33O5NS2.0.3 H2O) C, H, N.

Sources & evidence

ORD record
ord-a421540acc4f44e293863afa024d0e7f
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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