Lithium hydroxide, monohydrate → 4-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)-2-methylbutanoic acid

HRID 82378노트

반응식

HRID 82378 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:16])[C:12]([O:14]C)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([CH3:16])[C:12]([OH:14])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 67339056HCID 67339056, 화합물

생성물 1

HCID 673403054-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)-2-methylbutanoic acid수율 99%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-2-methylbutanoate (720 mg, 2.11 mmol) was dissolved in THF (4.2 mL) and water (1.8 mL). The mixture was treated with LiOH—H2O (265 mg, 6.32 mmol) and allowed to stir overnight to completion by LCMS analysis. The mixture was diluted with water and washed twice with diethyl ether (discarded). The aqueous was treated with 3M HCl solution until a pH of about 2 to about 3 (white ppt) and extracted with ethyl acetate several times. The combined organic portions were washed with water, then brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford 4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-2-methylbutanoic acid as a colorless oil (684 mg, 99%). LCMS (APCI+) [M+H]+326.0; Rt: 2.26 min.

후처리

  1. washwashed twice with diethyl ether (discarded)
  2. additionThe aqueous was treated with 3M HCl solution until a pH of about 2 to about 3 (white ppt)
  3. extractionextracted with ethyl acetate several times
  4. washThe combined organic portions were washed with water
  5. custombrine, separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-049d0f5d4e0643d9880d90294b1165aa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846681B2

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