Triethylamine → HCID 178446157, compound

HRID 1664568Notes

Reaction equation

HRID 1664568 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8]/[C:7]/1=[N:16]\[NH2:17])[CH2:2][CH2:3][CH2:4][CH3:5].[C:18]([NH:28][CH2:29][C:30](O)=[O:31])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[O:31]=[C:30]([NH:17]/[N:16]=[C:7]1\[NH:8][C:9](=[O:15])[C:10]2[NH:11][CH:12]=[N:13][C:14]=2[N:6]\1[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:29][NH:28][C:18](=[O:19])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14349BenzyloxycarbonylglycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178446164HCID 178446164, compound

Product 1

HCID 178446157HCID 178446157, compoundYield 144.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.50 g, 0.0021 mol), N-carbobenzyloxyglycine (0.49 g, 0.0023 mol), benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (1.0 g, 2.3 mmol) and triethylamine (0.59 mL, 0.0042 mol) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water (4×) and brine (1×). The aqueous was extracted with EtOAc (2×). The combined organic layers were dried (MgSO4) and concentrated to give the desired product (1.30 g, 86%). LCMS calculated for C20H26N7O4 (M+H): 428.2. found 428.2.

Workup

  1. washwashed with water (4×) and brine (1×)
  2. extractionThe aqueous was extracted with EtOAc (2×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e891e2d415fc4e649943d941e70bc6fc
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

Loading…