HCID 18463921, compound → HCID 18463943, compound

HRID 2231082Notes

Reaction equation

HRID 2231082 reaction equation
C([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH2:17][N:18]2[C:24](=[O:25])[CH:23]([NH:26][C:27](=[O:37])[C:28]3[CH:33]=[C:32]([Cl:34])[C:31]([OH:35])=[C:30]([Cl:36])[CH:29]=3)[CH2:22][CH2:21][C:20](=[O:38])[N:19]2[CH2:39][CH2:40][CH3:41])=[O:16])[CH2:12][C:11](=[O:42])[O:10]1)C1C=CC=CC=1.[CH2:43]([N:50]1[C:56](=[O:57])[CH2:55][CH2:54][CH:53]([NH:58][C:59]([C:61]2[C:70]3[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=3)[CH:64]=[CH:63][N:62]=2)=[O:60])[C:52](=[O:71])[N:51]1[CH2:72][C:73]([NH:75][CH:76]([CH:81]=[O:82])[CH2:77][C:78]([OH:80])=[O:79])=[O:74])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[Cl:36][C:30]1[CH:29]=[C:28]([CH:33]=[C:32]([Cl:34])[C:31]=1[OH:35])[C:27]([NH:26][CH:23]1[C:24](=[O:25])[N:18]([CH2:17][C:15]([NH:14][CH:13]([CH:9]=[O:8])[CH2:12][C:11]([OH:42])=[O:10])=[O:16])[N:19]([CH2:39][CH2:40][CH3:41])[C:20](=[O:38])[CH2:21][CH2:22]1)=[O:37].[CH2:43]([N:50]1[C:56](=[O:57])[CH2:55][CH2:54][CH:53]([NH:58][C:59]([C:61]2[C:70]3[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=3)[CH:64]=[CH:63][N:62]=2)=[O:60])[C:52](=[O:71])[N:51]1[CH2:72][C:73]([NH:75][CH:76]([CH:81]=[O:82])[CH2:77][C:78]([OH:80])=[O:79])=[O:74])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

4

Reactant 2

HCID 18463921HCID 18463921, compoundHCID 18463943HCID 18463943, compound

Product 2

HCID 18463943HCID 18463943, compoundYield 74%HCID 18463946HCID 18463946, compound

Procedure

3-{2-[6-(3,5-Dichloro-4-hydroxy-benzoylamino)-3,7-dioxo-2-propyl-[1,2]diazepan-1-yl]-acetylamino}-4-oxo-butyric acid (11c) was prepared from N-{2-[(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-3,7-dioxo-1-propyl-[1,2]diazepan-4-yl}-3,5-dichloro-4-hydroxy-benzamide (10d, diastereomers) (30 mg, 0.05 mmol) by the method used to prepare 11a to afford 19 mg (74% yield) of the title compound. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 mL/3 drops) δ 0.90-0.95 (t, 3H), 1.60-1.70 (m, 2H), 2.00-2.10 (m, 1H), 2.25-2.36 (m, 1H), 2.48-2.82 (m, 3H), 2.98-3.10 (m, 1H), 3.20-3.35 (m, 1H), 3.90-4.50 (m, 4H), 4.95-5.08 (m, 1H), 7.62-7.72 (m, 2H). Analytical HPLC: 5.40 min. LC-MS (ES+): m/e=531, 533 (M+H+).

Sources & evidence

ORD record
ord-2634141a7c7042a9898bc1f5836963fe
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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