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Ammonium Chloride → (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone

HRID 1050556
Notes
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Reaction equation

HRID 1050556 reaction equation
CON(C)[C:4](=[O:28])[C@H:5]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6][CH2:7][CH2:8][NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:30][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[CH2:13]([O:12][C:10]([NH:9][CH2:8][CH2:7][CH2:6][C@@H:5]([NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:4](=[O:28])[CH3:30])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 118114437N-methoxy-N-methyl-(R)-5-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)pentanamideHCID 178418689HCID 178418689, compound

Product 1

HCID 98005910(R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanoneYield 75%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-30 °C

Procedure

N-Methoxy-N-methyl-(R)-5-(Benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-pentanamide (305) (10 g, 24 mmol) was dissolved in THF (250 mL) and the solution was cooled to −30° C. in a dry-ice acetone bath. MeMgBr (3M in Et2O, 123 mL, 369 mmol) was added drop-wise over 30 minutes. The bath temperature was slowly allowed to increase to 0° C. and then was maintained at 0° C. until TLC showed no further reaction progress (˜80-90% complete). Saturated NH4Cl (aq) was then slowly added to the reaction mixture at 0° C. and the THF was removed under reduced pressure. The resulting aqueous solution was then extracted with EtOAc and the extracts were washed with water and then brine. The residue was then purified by column chromatography (EtOAc/hexanes) to give (R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone (306), (6.5 g, 18 mmol, 75% yield).

Workup

  1. temperatureto increase to 0° C.
  2. temperaturewas maintained at 0° C. until TLC
  3. customthe THF was removed under reduced pressure
  4. extractionThe resulting aqueous solution was then extracted with EtOAc
  5. washthe extracts were washed with water
  6. customThe residue was then purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-96670990d15e4bcc90f8296974acea66
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382246B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes