HCID 18463919, compound → HCID 18463919, compound
Reaction equation
[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]([N:19]2[C:25](=[O:26])[CH:24]([NH:27][C:28](=[O:38])[C:29]3[CH:34]=[C:33]([Cl:35])[C:32]([OH:36])=[C:31]([Cl:37])[CH:30]=3)[CH2:23][CH2:22][C:21](=[O:39])[N:20]2[CH3:40])[CH3:18])=[O:16])[CH2:12][C:11](=[O:41])[O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C(=O)CCC(NC(C2C3C(=CC=CC=3)C=CN=2)=O)C(=O)N1CC(NC(C=O)CC(O)=O)=O)C1C=CC=CC=1>>[Cl:37][C:31]1[CH:30]=[C:29]([CH:34]=[C:33]([Cl:35])[C:32]=1[OH:36])[C:28]([NH:27][CH:24]1[C:25](=[O:26])[N:19]([CH:17]([CH3:18])[C:15]([NH:14][CH:13]([CH:9]=[O:8])[CH2:12][C:11]([OH:41])=[O:10])=[O:16])[N:20]([CH3:40])[C:21](=[O:39])[CH2:22][CH2:23]1)=[O:38].[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]([N:19]2[C:25](=[O:26])[CH:24]([NH:27][C:28](=[O:38])[C:29]3[CH:30]=[C:31]([Cl:37])[C:32]([OH:36])=[C:33]([Cl:35])[CH:34]=3)[CH2:23][CH2:22][C:21](=[O:39])[N:20]2[CH3:40])[CH3:18])=[O:16])[CH2:12][C:11](=[O:41])[O:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
3-{2-[6-(3,5-Dichloro-4-hydroxy-benzoylamino)-2-methyl-3,7-dioxo-[1,2]diazepan-1-yl]-propionylamino}-4-oxo-butyric acid (20) was prepared from N-{2-[1-(2-benzyloxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-ethyl]-1-methyl-3,7-dioxo-[1,2]diazepan-4-yl}-3,5-dichloro-4-hydroxy-benzamide (19) (28 mg, 0.046 mmol) by the method used to prepare 11a, affording 17 mg (71% yield) of the title compound. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 mL/3 drops) δ 1.20-1.50 (m, 3H), 1.90-2.10 (m, 1H), 2.25-2.85 (m, 4H), 3.10-3.40 (m, 3H), 4.05-4.50 (m, 1H), 4.55-4.65 (m, 1H), 4.75-5.05 (m, 2H), 7.72-7.76 (m, 2H). Analytical HPLC: 7.51 min. LC-MS (ES+): m/e=517, 519 (M+H+).
Sources & evidence
- ORD record
- ord-160ebda7cb0747d2a9d5b4c4829c3454
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06426413B1
Reaction notes
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