4-Nitrophenyl chloroformate → HCID 57918966, compound

HRID 2266294Notes

Reaction equation

HRID 2266294 reaction equation
[NH2:1][C@@H:2]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C@@H:3]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:4][C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].C([O-])(O)=O.[Na+].Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:34]>CC#N>[CH2:8]([NH:7][C:5](=[O:6])[CH2:4][C@H:3]([O:12][Si:13]([C:16]([CH3:18])([CH3:17])[CH3:19])([CH3:14])[CH3:15])[C@@H:2]([NH:1][C:33](=[O:34])[O:35][C:36]1[CH:37]=[CH:38][C:39]([N+:42]([O-:44])=[O:43])=[CH:40][CH:41]=1)[CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 57918994HCID 57918994, compound

Product 1

HCID 57918966HCID 57918966, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of crude (3S,4S)-4-amino-N-butyl-3-(tertbutyldimethylsilyloxy)-5-cyclohexylpentanamide (311 mg, 0.81 mmol) in MeCN were added powdered NaHCO3 (203 mg, 2.43 mmol) and p-nitrophenyl chloroformate (244 mg, 1.21 mmol) and the mixture was stirred overnight at rt. The mixture was concentrated under reduced pressure. The residue was taken up in 1:1 EtOAc/Et2O (90 mL), washed with water (20 mL) and brine (20 mL), dried over MgSO4 and concentrated to leave an orange oil. This material was chromatographed on a 40-g silica cartridge eluted with a 0 to 100% ethyl acetate in hexanes gradient to afford 4-nitrophenyl (2S,3S)-5-(butylamino)-3-(tert-butyldimethylsilyloxy)-1-cyclohexyl-5-oxopentan-2-ylcarbamate (39 mg, 8%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto leave an orange oil
  6. customThis material was chromatographed on a 40-g silica cartridge
  7. washeluted with a 0 to 100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-2ed0a9bb6fec4f3ca0018381ef5039ce
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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