Ethanol → HCID 178448380, compound

HRID 1455145Notes

Reaction equation

HRID 1455145 reaction equation
[C:1]([NH:8][C@@H:9]([C:13]([NH2:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.C([O+](CC)CC)C.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCO>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:13](=[NH:15])[NH:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:10]([CH3:12])[CH3:11])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 7504BenzylamineHCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 10856902Boc-D-Valine amide

Product 1

HCID 178448380HCID 178448380, compoundYield 201.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Boc-D-Valine amide (10 g, 46 mMol) in CH2Cl2 (200 mL) was added Triethyloxonium hexafluorophosphate (13.0 g, 48 mMol). (The reaction started out as a suspension which gradually cleared.) The reaction was stirred for 48 h at RT, poured into a separatory funnel, washed with 1 N Na2CO3, dried (Na2SO4), filtered and concentrated under vacuum. To the remaining oil was added Benzylamine (5.0 mL, 23 mMol) and EtOH (20 mL). The reaction was stirred at 60° C. for 24 h. After cooling to RT the reaction was evaporated under vacuum. The title compound (14.16 g, >95% pure by LCMS) was obtained without purification as a pale yellow oil which eventually solidified to a waxy solid: MS (ES) m/e 306.4 (M+H)+.

Workup

  1. additionpoured into a separatory funnel
  2. washwashed with 1 N Na2CO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. stirringThe reaction was stirred at 60° C. for 24 h
  7. temperatureAfter cooling to RT the reaction
  8. customwas evaporated under vacuum

Sources & evidence

ORD record
ord-6bd142d98de64d57ab15caeafc5362f1
Source dataset
uspto-grants-2009_01
Patent number
US07482343B2

Reaction notes

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