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Phosphoric Acid → (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid

HRID 588295
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HRID 588295 반응식
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:11][C:10](=[CH2:26])[C:9]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].P(=O)(O)(O)[OH:31]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:19][C:14]([CH2:13][C@@H:12]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][C:10](=[CH2:26])[C:9]([OH:27])=[O:31])=[CH:15][CH:16]=1
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7

반응물 3

HCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 46193438(R)-5-Biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butylester

생성물 1

HCID 46193439(R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매
HCID 962
Water
용매
2회
HCID 8028Tetrahydrofuran용매

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온도
10 °C

실험 절차

(R)-5-Biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (4-a, R1=Boc) (27.7 g) is dissolved in THF (270 ml) at room temperature. Tetrabutylammonium bromide (0.24 g) is added followed with water (10 ml). The mixture is then cooled to 10° C. A solution of lithium hydroxide (7.3 g) in water (92 ml) is added over 2 h. Phosphoric acid (37 g, 85%) is added until pH 3. Phases are then separated. The organic phase is diluted with toluene (100 ml) and washed with brine. Phases are separated. The organic phase is then concentrated in vacuo. The residue is dissolved in acetonitrile (350 ml) at 80° C. and azeotropically distilled. Further acetonitrile is added (150 ml) and the mixture cooled to 0° C. The solid is collected by filtration and dried, to afford (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid (2-a, R1=Boc, R2=H, R3=CO2H) (25.7 g). δH (400 MHz, DMSO) 1.30 (9H), 2.29 (1H), 2.50 (1H), 2.75 (2H), 3.91 (8H), 5.62 (1H), 6.09 (1H), 6.66 (1H), 7.28 (2H), 7.33 (1H), 7.44 (2H), 7.56 (2H), 7.63 (2H).

후처리

  1. customPhases are then separated
  2. additionThe organic phase is diluted with toluene (100 ml)
  3. washwashed with brine
  4. customPhases are separated
  5. concentrationThe organic phase is then concentrated in vacuo
  6. dissolutionThe residue is dissolved in acetonitrile (350 ml) at 80° C.
  7. distillationazeotropically distilled
  8. additionFurther acetonitrile is added (150 ml)
  9. temperaturethe mixture cooled to 0° C
  10. filtrationThe solid is collected by filtration
  11. customdried

출처 및 근거

ORD 기록
ord-49a56b7f75334966824c2f60d5ebccca
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09227934B2

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