Hydrochloric Acid → Boc-4-bromo-D-phenylalanine methyl ester

HRID 1469675노트

반응식

HRID 1469675 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:21]([O-])([O-])=O.[Cs+].[Cs+].IC.Cl>CN(C=O)C>[CH3:21][O:11][C:10](=[O:12])[C@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 7020327(2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

생성물 1

HCID 15735974Boc-4-bromo-D-phenylalanine methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (R)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid (1.0 g, 2.91 mmol) in DMF (5 mL) is added Cs2CO3 (1.041 g, 3.2 mmol) and the mixture is stirred at room temperature for 30 minutes. Then iodomethane (1.031 g, 7.26 mmol) is added and the mixture is stirred at room temperature about 72 hours. The pH is adjusted to 5˜6 by adding 1N HCl then the mixture is extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated to give (R)-3-(4-bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester. HPLC Retention time 1.49 minutes (condition C): MS 358.3 (M−1).

후처리

  1. stirringthe mixture is stirred at room temperature about 72 hours
  2. extractionthe mixture is extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7f22d50b83ea491fa613b6318b34772c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006249B2

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