4-Hydroxybenzaldehyde → HCID 58781797, compound

HRID 1373673Notes

Reaction equation

HRID 1373673 reaction equation
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:28]([O:32][C:33]([NH:35][C@H:36]([C:41]([OH:43])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])([CH3:31])([CH3:30])[CH3:29].O[C:45]1[CH:52]=[CH:51][C:48]([CH:49]=[O:50])=[CH:47][CH:46]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.ClCCl>[CH:49]([C:48]1[CH:51]=[CH:52][C:45]([O:42][C:41](=[O:43])[CH:36]([NH:35][C:33]([O:32][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:34])[CH2:37][CH:38]([CH3:39])[CH3:40])=[CH:46][CH:47]=1)=[O:50]

Participants

8

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 58781797HCID 58781797, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

BOP (13.0 mmol) was added to a solution of N-tert-butyloxycarbonyl-L-leucine (10.9 mmol) and 4-hydroxybenzaldehyde (13.0 mmol) in dry DMF (12 mL), and stirred to dissolve. N,N-Diisopropylethylamine (43.0 mmol) and 4-dimethylaminopyridine (1 mmol) were added with stirring. The resulting solution was stirred for 2.5 hours. The reaction mixture was covered with dichloromethane (100 mL) and washed with water, saturated aqueous sodium bicarbonate, and saturated brine. The dichloromethane was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The resulting red oil was purified by column chromatography on silica gel with dichloromethane as an eluant.

Workup

  1. dissolutionto dissolve
  2. stirringwith stirring
  3. stirringThe resulting solution was stirred for 2.5 hours
  4. washwashed with water, saturated aqueous sodium bicarbonate, and saturated brine
  5. dry with materialThe dichloromethane was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting red oil was purified by column chromatography on silica gel with dichloromethane as an eluant

Sources & evidence

ORD record
ord-6f39a02fc70347b0ab80c616c7c0e8fa
Source dataset
uspto-grants-2007_01
Patent number
US07163923B2

Reaction notes

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