Triethylamine → HCID 19091322, compound

HRID 487866Notes

Reaction equation

HRID 487866 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:30])[CH:16]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=1)[NH2:17])[CH3:13].C(N(CC)CC)C>O1CCOCC1>[CH2:12]([O:14][C:15](=[O:30])[CH:16]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:20]=1)[NH:17][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 19091324HCID 19091324, compound

Product 1

HCID 19091322HCID 19091322, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

At 10°-15° C., add benzylchloroformate (15.5 mL) dropwise to a heterogeneous mixture of 3-methanesulfonamido-D,L-phenylalanine ethyl ester (25.00 g) and triethylamine (15 mL) in dioxane (400 mL). Warm to room temperature, stir overnight, and remove the dioxane in vacuo. Partition the mixture between EtOAc (200 mL)/water (500 mL). Wash the EtOAc solution with water (500 mL), 1N HCl (500 mL), 5% NaHCO3 (500 mL), and brine (500 mL). Concentrate the dried (MgSO4) EtOAc solution in vacuo to a residue. Chromatograph the residue on silica gel (40μ, 2200 mL) using EtOAc:hexane (3:7) as eluant to give N-benzyloxycarbonyl-3-methanesulfonamido-D,L-phenylalanine ethyl ester.

Workup

  1. customremove the dioxane in vacuo
  2. customPartition the mixture between EtOAc (200 mL)/water (500 mL)
  3. washWash the EtOAc solution with water (500 mL), 1N HCl (500 mL), 5% NaHCO3 (500 mL), and brine (500 mL)
  4. concentrationConcentrate the
  5. dry with materialdried (MgSO4) EtOAc solution in vacuo to a residue

Sources & evidence

ORD record
ord-58c9a8df60134292a87788eccdc45c66
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

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