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Triethylamine → HCID 178446157, compound

HRID 2368606
Notes
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Reaction equation

HRID 2368606 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 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-c2a9ad5667ad4ee98e92e284a3c5b55a
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08703783B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes