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

HRID 2093009Notes

Reaction equation

HRID 2093009 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]

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-c89d013ba25e4197a1daef65dd2fe5d1
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

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