2-(2,4-Dioxoimidazolidin-1-yl)acetic acid hydrochloride → (S)-3-(benzyloxy)-2-(2-(2,4-dioxoimidazolidin-1-yl)acetamido)-N-(4-phenoxyphenyl)propanamide

HRID 1630093Notes

Reaction equation

HRID 1630093 reaction equation
Cl.[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH2:5][N:4]1[CH2:9][C:10]([OH:12])=O.[NH2:13][C@@H:14]([CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)=[O:16]>>[CH2:33]([O:32][CH2:31][C@H:14]([NH:13][C:10](=[O:12])[CH2:9][N:4]1[CH2:5][C:6](=[O:8])[NH:7][C:3]1=[O:2])[C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:22][CH:23]=1)=[O:16])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 670091652-(2,4-Dioxoimidazolidin-1-yl)acetic acid hydrochlorideHCID 67009331(S)-2-amino-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide

Product 1

HCID 67009280(S)-3-(benzyloxy)-2-(2-(2,4-dioxoimidazolidin-1-yl)acetamido)-N-(4-phenoxyphenyl)propanamideYield 45%

Procedure

Proceeding as in Example 1, but substituting 2-(2,4-dioxoimidazolidin-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-phenoxyphenyl)propanamide, gave Compound 201, (S)-3-(benzyloxy)-2-(2-(2,4-dioxoimidazolidin-1-yl)acetamido)-N-(4-phenoxyphenyl)propanamide (54.1 mg, 45%). 1H-NMR (400 MHz, DMSO-D6): σ 10.62 (d, 1H), 10.15 (d, 1H), 8.47-8.41 (m, 1H), 7.83 (d, 1H), 7.65-7.61 (m, 2H), 7.39-7.26 (m, 6H), 7.10 (t, 1H), 7.02-6.96 (m, 4H), 4.73-4.66 (m, 1H), 4.53 (s, 2H), 4.25-4.20 (m, 1H), 3.71-3.63 (m, 2H), 2.73-2.63 (m, 1H). MS (EI) for C27H26N4O6. found 503.1 (MH+).

Sources & evidence

ORD record
ord-6d36ac0a525941009fefee89829b9d47
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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