Acetic Acid → tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate

HRID 1394010Notes

Reaction equation

HRID 1394010 reaction equation
Cl.[NH2:2][C:3]1[NH:4][CH2:5][CH2:6][CH2:7][N:8]=1.CC(C)([O-])C.[K+].[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][NH:35][C:36](=[O:49])[C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][C:45](OC)=[O:46])=[CH:39][CH:38]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>CN(C=O)C>[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][NH:35][C:36](=[O:49])[C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][C:45](=[O:46])[NH:2][C:3]2[NH:8][CH2:7][CH2:6][CH2:5][N:4]=2)=[CH:39][CH:38]=1)[C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15512203tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionateHCID 225575271,3-Diazinan-2-imine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 15512204tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)ethyl)benzoylamino)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.25 g (9.2 mmol) of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride and 1.03 g (9.2 mmol) of potassium tert-butoxide were dissolved in 3 ml of absol. DMF and the mixture was stirred at RT for 30 min. 740 mg (1.53 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate (Example 3c) in 1 ml of DMF were then added and the mixture was stirred at RT for 4 h. It was adjusted to pH 4 using glacial acetic acid, the solvent was stripped off in vacuo, and the residue was chromatographed on silica gel (dichloromethane/methanol/glacial acetic acid/water (9/1/0.1/0.1)). Yield: 190 mg (38%). MS: ES+, m/e=552.3 (M+H+, 100%)

Workup

  1. customthe residue was chromatographed on silica gel (dichloromethane/methanol/glacial acetic acid/water (9/1/0.1/0.1))

Sources & evidence

ORD record
ord-d77fcdc7cbcc41b1baa845741fbce615
Source dataset
uspto-grants-2008_03
Patent number
US07348333B2

Reaction notes

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