Triethylamine → HCID 19091322, 화합물

HRID 487866노트

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HRID 487866 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 19091324HCID 19091324, 화합물

생성물 1

HCID 19091322HCID 19091322, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58c9a8df60134292a87788eccdc45c66
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298492

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