HCID 69686346, compound → HCID 69686346, compound

HRID 2231086Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:28])[CH:5]([N:7]1[C:13](=[O:14])[CH:12]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH2:11][CH2:10][C:9](=[O:26])[N:8]1[CH3:27])[CH3:6])[CH3:2].C(OC(=O)CN1C(=O)C(N)CCC(=O)N1CC1C=CC=CC=1)(C)(C)C>>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([N:7]1[C:13](=[O:14])[CH:12]([NH2:15])[CH2:11][CH2:10][C:9](=[O:26])[N:8]1[CH3:27])[CH3:6])[CH3:2].[CH2:1]([O:3][C:4](=[O:28])[CH:5]([N:7]1[C:13](=[O:14])[CH:12]([N:15]2[C:16](=[O:25])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]2=[O:24])[CH2:11][CH2:10][C:9](=[O:26])[N:8]1[CH3:27])[CH3:6])[CH3:2]

Participants

Reactant 2

HCID 69686346HCID 69686346, compound

HCID 69686539HCID 69686539, compound

Product 2

HCID 54386283HCID 54386283, compound

HCID 69686346HCID 69686346, compoundYield 73%

Procedure

2-(6-Amino-2-methyl-3,7-dioxo-[1,2]diazepan-1-yl)-propionic acid ethyl ester (16) was prepared from 2-[6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-3,7-dioxo-[1,2]diazepan-1-yl]-propionic acid ethyl ester (15) by the method used to prepare 6a to afford 143 mg (73% yield) of the title compound as a mixture of diastereomers. 1H-NMR (500 MHz, CDCl3) δ 1.22-1.30 (m, 2.5H), 1.47-1.50 (d, 0.5H), 1.52-1.70 (m, 3H), 1.70-1.82 (m, 1H), 2.30-2.40 (m, 1H), 2.48-2.69 (m, 1H), 2.75-2.82 (m, 0.5H), 3.03-3.11 (m, 0.5H), 3.22 (d, 3H), 3.61-3.75 (m, 1H), 4.18-4.30 (m, 2H), 4.49-4.54 (m, 0.5H), 4.85-4.90 (m, 0.5H). Analytical HPLC: 3.90 and 4.06 min. LC-MS (ES+): m/e=258 (M+H+).

Sources & evidence

ORD record: ord-3d549ec0b68d4d808092c8f98ac98e53
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426413B1

Reaction notes

Loading…