Benzyl chloroformate → HCID 70986729, compound

HRID 2099703Notes

Reaction equation

HRID 2099703 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([CH:9]([CH3:22])[CH2:10][C:11]1[CH:21]=[CH:20][C:14]2[O:15][CH:16]([CH2:18][NH2:19])[O:17][C:13]=2[CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35]>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:23])[N:7]([CH:9]([CH3:22])[CH2:10][C:11]1[CH:21]=[CH:20][C:14]2[O:15][CH:16]([CH2:18][NH:19][C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[O:17][C:13]=2[CH:12]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 70986723HCID 70986723, compound

Product 1

HCID 70986729HCID 70986729, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.31 g (0.96 mmol) of 1F in 5 mL of dichloromethane was added 0.2 mL (1.14 mmol) of N,N-diisopropylethylamine and 10 mg (0.08 mmol) of 4-dimethylaminopyridine (4-DMAP) followed by 0.15 mL of benzyl chloroformate (1.04 mmol) at room temperature. The mixture was allowed to stir for 1 hours and concentrated to dryness under reduced pressure. The residue was purified by silica gel flash column chromatography using 40% ethyl acetate in hexane to give 0.41 g (0.89 mmol, 94%) of 1G as a thick colorless gum (M+Na, 479).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-2b9995d1cf7349baabefb3bfad784278
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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