Hydroxyacetone → HCID 13993751, compound

HRID 1970565Notes

Reaction equation

HRID 1970565 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O[CH2:20][C:21](=[O:23])[CH3:22].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[O:23]=[C:21]([CH3:22])[CH2:20][O:4][C:3]([C@@H:2]1[CH2:6][CH2:7][CH2:8][N:1]1[C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])=[O:5]

Participants

6

Reactant 3

HCID 8299HydroxyacetoneHCID 10868DicyclohexylcarbodiimideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 13993751HCID 13993751, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.0 g Z-Pro-OH n 20 ml dichloromethane were added 0.58 ml hydroxyl-acetone and 10 mg DMAP. The solution was cooled to 0° C. and a solution of 1.7 g DCC in 20 ml dichloromethane was added dropwise. The suspension was allowed to warm to RT for 16 h before being filtered over a short plug of Celite. The reaction mixture was washed with dichloro-methane and the combined wash solutions evaporated. The residue thus obtained was purified by chromatography on silica using heptane/ethyl acetate 1:1 as eluent.

Workup

  1. temperatureto warm to RT for 16 h
  2. filtrationbefore being filtered over a short plug of Celite
  3. washThe reaction mixture was washed with dichloro-methane
  4. customthe combined wash solutions evaporated
  5. customThe residue thus obtained
  6. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-7cd46a1522f44b68ae21d50c8a7271b3
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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