Dimethylformamide → Tert-butyl (2s)-2benzyloxycarbonylamino-3-(4-(3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)propyloxy)phenyl)propionate

HRID 2297384Notes

Reaction equation

HRID 2297384 reaction equation
CC(C)([O-])C.[K+].Cl.N[N:9]1[CH2:14][CH2:13][CH2:12][N:11]=[CH:10]1.[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][C:45]([O:47]CC)=O)=[CH:37][CH:36]=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[N:51](C)C=O>>[CH2:15]([O:22][C:23]([NH:25][C@@H:26]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][C:45](=[O:47])[NH:51][C:10]2[NH:9][CH2:14][CH2:13][CH2:12][N:11]=2)=[CH:37][CH:36]=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

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11038228tert-Butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionateHCID 183815871-Amino-1,4,5,6-tetrahydropyrimidine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 57146332Tert-butyl (2s)-2benzyloxycarbonylamino-3-(4-(3-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)propyloxy)phenyl)propionateYield 60.6%

Procedure

6.72 g (0.06 mol) of potassium tert-butoxide were added to a solution of 8.13 g (0.06 mol) of 1-amino-1,4,5,6-tetrahydropyrimidine hydrochloride in 100 ml of absolute dimethylformamide. After stirring at room temperature for 30 min, 7.2 g (0.015 mol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate were added to this solution and it was stirred at room temperature for 12 h. After removal of the solvent in vacuo, the residue was treated with 300 ml of ethyl acetate and 100 ml of water, and the organic phase was separated off, washed two times with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product thus obtained was immediately chromatographed on silica gel (dichloromethane/methanol/glacial acetic acid 10015/1). 5.4 g (60.6%) of amorphous product were obtained.

Workup

  1. stirringwas stirred at room temperature for 12 h
  2. customAfter removal of the solvent in vacuo
  3. additionthe residue was treated with 300 ml of ethyl acetate and 100 ml of water
  4. customthe organic phase was separated off
  5. washwashed two times with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product thus obtained
  9. customwas immediately chromatographed on silica gel (dichloromethane/methanol/glacial acetic acid 10015/1)

Sources & evidence

ORD record
ord-790586bdf8fe4ee6b5217969ec54d62c
Source dataset
uspto-grants-2002_12
Patent number
US06492356B1

Reaction notes

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