Bicarbonate Ion → (2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate

HRID 926940

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HRID 926940 반응식
[C:1]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N+]([CH2:35][CH2:36][CH2:37][CH3:38])(CCCC)CCCC)CCC.[C:39](N[C@@H](CC1C=C(O)C(O)=CC=1)C(O)=O)([O:41][C:42](C)([CH3:44])[CH3:43])=[O:40].C(=O)(O)[O-].CN1CC[CH2:67][C:66]1=O>C(OC)(C)(C)C>[OH:20][C:19]1[CH:21]=[C:14]([CH2:13][C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[C:10]([O:12][CH2:43][C@H:42]([O:41][C:39]([C:38]2[CH:37]=[CH:36][CH:35]=[CH:67][CH:66]=2)=[O:40])[CH3:44])=[O:11])[CH:15]=[CH:16][C:17]=1[OH:18]

참가 물질

6

반응물 4

HCID 769Bicarbonate IonHCID 13387N-methyl-2-pyrrolidoneHCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanineHCID 131728417Boc-L-dopa tetrabutylammonium salt

생성물 1

HCID 46899463(2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
100 °C

실험 절차

Boc-Dopa TBA salt 3 (50 g, 93 mmol), bicarbonate-washed (1R)-2-chloroisopropyl benzoate 5 (20 g, 100 mmol), and N-methylpyrrolidinone (NMP) (100 mL) were added to a 250 mL round bottom flask. The mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 100° C. After ca. 72 hrs the reaction was cooled to room temperature, diluted with tert-butyl methylether (MTBE) (1 L), and washed twice with deionized water (2 L, then 1 L). The organic phase was separated, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to provide 35 g (76 mmol) of (2R)-2-phenylcarbonyloxypropyl(2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate 6 as a tan, viscous oil.

후처리

  1. additionwere added to a 250 mL round bottom flask
  2. temperatureAfter ca. 72 hrs the reaction was cooled to room temperature
  3. washwashed twice with deionized water (2 L
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ac6d7a3090f84f31b3a45f1c609b470a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290445B2

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