Ethylmorpholine → 1-methyl-N-(1-naphthalenylmethyl)-5-oxoprolinamide

HRID 554129노트

반응식

HRID 554129 반응식
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][C@H:3]1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.[C:41]1([CH2:51][NH2:52])[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1>ClCCl>[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][CH2:7][C@H:3]1[C:4]([NH:52][CH2:51][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][CH:42]=1)=[O:6]

참가 물질

7

반응물 5

HCID 7525EthylmorpholineHCID 83551-NaphthalenemethanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18649403(2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acid

생성물 1

HCID 674600911-methyl-N-(1-naphthalenylmethyl)-5-oxoprolinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-methyl-5-oxoproline (0.050 g, 0.35 mmol, prepared in a manner analogous to that described above for example 51), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.081 g, 0.42 mmol), 1-hydroxybenzotriazole (0.057 g, 0.42 mmol), N-ethyl morpholine (0.166 ml, 1.05 mmol) and (1-naphthalenylmethyl)amine were combined in dichloromethane (˜8 ml) and the mixture was stirred for ˜20 hrs at room temperature. The mixture was then washed with 2M aqueous hydrogen chloride (5 ml) and the organic layer was separated using a phase separator. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, separated as before, and then evaporated. The residue was purified by mass-directed automated HPLC to give pure 1-methyl-N-(1-naphthalenylmethyl)-5-oxoprolinamide as a white solid (0.062 g).

후처리

  1. washThe mixture was then washed with 2M aqueous hydrogen chloride (5 ml)
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  4. customseparated as before, and
  5. customthen evaporated
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-a380b0866e184bcb9e2515ba9b82ce2d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048907B2

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