HCID 22956504, compound → HCID 18463939, compound

HRID 2231078Notes

Reaction equation

HRID 2231078 reaction equation
C(O[C:6](=[O:35])[CH2:7][N:8]1[C:14](=[O:15])[CH:13]([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([O:25][CH2:26][CH:27]=[CH2:28])=[C:20]([Cl:29])[CH:19]=2)[CH2:12][CH2:11][C:10](=[O:31])[N:9]1[CH2:32][CH2:33][CH3:34])(C)(C)C.[CH2:36]([N:43]1[C:49](=[O:50])[CH2:48][CH2:47][CH:46]([NH:51][C:52]([C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:57]=[CH:56][N:55]=2)=[O:53])[C:45](=[O:64])[N:44]1[CH2:65][C:66](=[O:82])[NH:67][CH:68]1[CH2:72][C:71](=[O:73])[O:70][CH:69]1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH2:26]([O:25][C:21]1[C:22]([Cl:24])=[CH:23][C:18]([C:17]([NH:16][CH:13]2[CH2:12][CH2:11][C:10](=[O:31])[N:9]([CH2:32][CH2:33][CH3:34])[N:8]([CH2:7][C:6](=[O:35])[NH:67][CH:68]3[CH2:72][C:71](=[O:73])[O:70][CH:69]3[O:74][CH2:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)[C:14]2=[O:15])=[O:30])=[CH:19][C:20]=1[Cl:29])[CH:27]=[CH2:28].[CH2:36]([N:43]1[C:49](=[O:50])[CH2:48][CH2:47][CH:46]([NH:51][C:52]([C:54]2[C:63]3[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH:57]=[CH:56][N:55]=2)=[O:53])[C:45](=[O:64])[N:44]1[CH2:65][C:66](=[O:82])[NH:67][CH:68]1[CH2:72][C:71](=[O:73])[O:70][CH:69]1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 22956504HCID 22956504, compoundHCID 57097701HCID 57097701, compound

Product 2

HCID 18463939HCID 18463939, compoundHCID 22956504HCID 22956504, compound

Procedure

4-Allyloxy-N-{2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-1-propyl-[1,2]diazepan-4-yl}-3,5-dichloro-benzamide (10c) was synthesized from 7c and the diastereomers of 9 by the method and chromatography used to prepare 10a to afford both anti diastereomer (78 mg, 31% yield, lower Rf) and syn diastereomer (129 mg, 52% yield, higher Rf) of the title compound. 1H-NMR (500Hz, CDCl3) for the anti diastereomer: δ 1.00-1.05 (t, 3H), 1.60-1.80 (m, 2H), 2.03-2.18 (m, 1H), 2.23-2.30 (d, 1H), 2.40-2.48 (m, 1H), 2.62-2.78 (m, 1H), 2.90-3.12 (m, 2H), 3.50-3.60 (m, 1H), 4.05-4.25 (m, 3H), 4.48-4.52 (m, 1H), 4.60-4.68 (m, 3H), 4.80-44.85 (d, 1H), 5.08-5.20 (m, 1H), 5.30-5.39 (m, 2H), 5.40-5.45 (d, 1H), 6.08-6.20 (m, 1H), 6.82-6.85 (d, 1H), 7.30-7.45 (m, 6H), 7.85 (s, 2H); for the syn diastereomer: δ 0.94-1.04 (t, 3H), 1.60-1.72 (m, 2H), 1.85-1.93 (m, 1H), 2.31-2.40 (m, 1H), 2.41-2.51 (m, 1H), 2.72-2.82 (m, 1H), 2.83-2.95 (m, 1H), 3.00-3.09 (m, 1H), 3.17-3.30 (m, 1H), 3.99-4.10 (m, 1H), 4.10-4.18 (d, 1H), 4.21-4.30 (d, 1H), 4.58-4.65 (m, 3H), 4.70-4.78 (m, 1H), 4.85-4.90 (d, 1H), 5.05-5.15 (m, 1H), 5.28-5.35 (d, 1H), 5.40-5.45 (d, 1H), 5.53 (d, 1H), 6.08-6.17 (m, 1H), 6.55-6.60 (d, 1H), 6.75-6.80 (d, 1H), 7.27-7.40 (m, 3H), 7.40-7.55 (m, 1H), 7.60-7.70 (m, 1H), 7.73 (s, 2H). Analytical HPLC for diastereomers of the title compound: 10.26 min. LC-MS (ES+) for the mixture of the product: m/e=661, 663 (M+H+).

Sources & evidence

ORD record
ord-d7d87cd9730f45b0bcb7c9f0e287e61a
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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