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Dimethylbarbituric acid → 3-Amino-N-cyclopropyl-2-hydroxyhexanamide

HRID 1015949
Notes
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Reaction equation

HRID 1015949 reaction equation
[CH:1]1([NH:4][C:5](=[O:19])[CH:6]([OH:18])[CH:7]([NH:11]C(=O)OCC=C)[CH2:8][CH2:9][CH3:10])[CH2:3][CH2:2]1.CN1C(=O)CC(=O)N(C)C1=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[NH2:11][CH:7]([CH2:8][CH2:9][CH3:10])[CH:6]([OH:18])[C:5]([NH:4][CH:1]1[CH2:2][CH2:3]1)=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 67246609Allyl 1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamate

Product 1

HCID 208049823-Amino-N-cyclopropyl-2-hydroxyhexanamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl 1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamate bound resin M1B (30 g, 1.0 eq.) was swollen with DCM. 1,3-Dimethylbarbituric acid (24.17 g, 12 eq.) and tetrakis(triphenylphosphine)palladium (1.49 g, 0.1 eq.) were added and the mixture shaken overnight. The mixture was filtered and washed with DMF and DCM to yield the resin M1D.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with DMF and DCM
  3. customto yield the resin M1D

Sources & evidence

ORD record
ord-324731ce9ab14cf593214588bc8eda02
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07985762B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes