Hydrochloric Acid → (2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid

HRID 2285380노트

반응식

HRID 2285380 반응식
C[O:2][C:3](=[O:33])[C@@H:4]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:5]([O:7][Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:29]([O:28][C:26]([NH:25][C@@H:4]([C@H:5]([O:7][Si:8]([C:21]([CH3:22])([CH3:24])[CH3:23])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[C:3]([OH:33])=[O:2])=[O:27])([CH3:30])([CH3:31])[CH3:32]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 10719205(2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

생성물 1

HCID 86709669(2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid수율 98.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

(2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (3.56 g, 7.55 mmol) was taken up in a mixture of tetrahydrofuran (10 mL) and water (3 mL) and cooled using an ice bath. Lithium hydroxide monohydrate (1.27 g, 30.2 mmol) was then added and the reaction was left to stir overnight. The solution was acidified using hydrochloric acid (2 M) until the solution was pH 2. The solution was then extracted with ethyl acetate. The organics were dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (3.41 g, 98%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.02-1.11 (m, 21H), 4.26-4.35 (m, 1H), 4.41-4.51 (m, 1H), 5.34 (d, J=9.0 Hz, 1H), 7.35-7.49 (m, 6H), 7.63-7.77 (m, 4H). LCMS (m/z) 458.1 [M+H], Tr=3.68 min.

후처리

  1. temperaturecooled
  2. waitthe reaction was left
  3. extractionThe solution was then extracted with ethyl acetate
  4. dry with materialThe organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3f07dc7b66014dc0958a751b41ac0956
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145441B2

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