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

HRID 387209Notes

Reaction equation

HRID 387209 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-cd9ae10048de4e749cb4984e10259df2
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

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