Dimethylformamide → HCID 67497618, compound

HRID 1628226Notes

Reaction equation

HRID 1628226 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[NH2:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([C@@H](CC1C=CC=CC=1)C(O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH:40]([N:43](C(C)C)CC)([CH3:42])[CH3:41].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=2N=N1.CN(C=[O:77])C>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:11][C:10]=1[NH:21][C:41](=[O:77])[C@@H:40]([NH:43][C:27](=[O:28])[O:26][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:42][C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67089511HCID 67089511, compoundHCID 67497584HCID 67497584, compound

Product 1

HCID 67497618HCID 67497618, compoundYield 35%

Procedure

To a solution of 2-(benzyloxy)-5-bromobenzenamine 13.D (1.59 g, 5.76 mmol) in DMF (20 mL) was added (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (1.83 g, 6.91 mmol, available from Aldrich), diisopropylethylamine (1.50 mL, 8.64 mmol) and 2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium hexafluorophosphate (2.62 g, 6.91 mmol). The resulting mixture is stirred overnight at room temperature. The mixture was then partitioned between water and EtOAc, the organic layer was separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-100% EtOAc/hexane) to afford tert-butyl (S)-1-(3-(1H-pyrazol-4-yl)phenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 13.E (1.25 g, 35% yield).

Workup

  1. customThe mixture was then partitioned between water and EtOAc
  2. customthe organic layer was separated
  3. extractionthe aqueous phase was extracted with additional EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography (0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-be7355156e384ead95f733db56a0721c
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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