Dicyclohexylcarbodiimide → HCID 118445527, compound

HRID 1486450Notes

Reaction equation

HRID 1486450 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])[CH3:3].[CH3:23][C:24]1([CH3:32])[O:31][C:29](=[O:30])[CH2:28][C:26](=[O:27])[O:25]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:23][C:24]1([CH3:32])[O:31][C:29](=[O:30])[CH:28]([C:20](=[O:22])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[C:26](=[O:27])[O:25]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 118445527HCID 118445527, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

DMAP (106 g, 0.86 mol) was added to a solution of Boc-L-4-nitro-Phenylalanine (1800 g, 0.58 mol) and Meldrum's acid (92 g, 0.64 mol) in dichloromethane (1.5 L). The resulting solution was cooled at −5° C. under N2 atmosphere, followed by addition of DCC (240 g, 1.16 mol) in dichloromethane (1 L) over 1 h. The mixture was stirred overnight at 0˜5° C. Then the precipitated N, N′-dicyclohexylurea was removed by filtration and the filtrate was washed with 5% aqueous HCl (1 L×3), and brine (1 L×1), and was dried over MgSO4. After removal of MgSO4 by filtration, the organic phase was concentrated to dryness. The residue was triturated with EtOAc/hexane (1:1, 500 mL), and was dried to afford tert-butyl (S)-(1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3-(4-nitrophenyl)-1-oxopropan-2-yl)carbamate (130.0 g, 51% yield) as a yellow solid.

Workup

  1. customThen the precipitated N, N′-dicyclohexylurea was removed by filtration
  2. washthe filtrate was washed with 5% aqueous HCl (1 L×3), and brine (1 L×1)
  3. dry with materialwas dried over MgSO4
  4. customAfter removal of MgSO4
  5. filtrationby filtration
  6. concentrationthe organic phase was concentrated to dryness
  7. customThe residue was triturated with EtOAc/hexane (1:1, 500 mL)
  8. customwas dried

Sources & evidence

ORD record
ord-5705073a8e834863951f56ebfb3c2d67
Source dataset
uspto-grants-2016_08
Patent number
US09427479B2

Reaction notes

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