1,3-Diazinan-2-imine hydrochloride → Tert-butyl (2s)-2-benzyloxycarbonylamino-3-(4-((1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)methyloxy)benzoylamino)propionate

HRID 2297389Notes

Reaction equation

HRID 2297389 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31](OC)=[O:32])=[CH:25][CH:24]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl.[NH2:43][C:44]1[NH:45][CH2:46][CH2:47][CH2:48][N:49]=1>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31](=[O:32])[NH:43][C:44]2[NH:49][CH2:48][CH2:47][CH2:46][N:45]=2)=[CH:27][CH:28]=1)[C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 225575271,3-Diazinan-2-imine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 56996374Tert-butyl (2s)-2-(benzyloxycarbonylamino)-3-(4-(methoxycarbonylmethyloxy)benzoylamino)propionate

Product 1

HCID 57208730Tert-butyl (2s)-2-benzyloxycarbonylamino-3-(4-((1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)methyloxy)benzoylamino)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

438 mg of tert-butyl (2S)-2-(benzyloxycarbonylamino)-3-(4-(methoxycarbonylmethyloxy)benzoylamino)propionate, 606 mg of potassium tert-butoxide and 732 mg of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride were dissolved in 10 ml of absolute dimethylformamide, and the solution was stirred at room temperature for 14 h and then concentrated to dryness in vacuo.

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-4d830e6a73ff4f618f44c74ddf97ed51
Source dataset
uspto-grants-2002_12
Patent number
US06492356B1

Reaction notes

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