Sodium Hydroxide → (3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide

HRID 750377

반응식

HRID 750377 반응식
C([O:9][CH:10]([C:27]([NH:29][C@@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:31])=[O:28])[C@@H:11]([NH:16]C(OCC1C=CC=CC=1)=O)[CH2:12][CH2:13][CH2:14][CH3:15])(=O)C1C=CC=CC=1.[OH-].[Na+]>O1CCOCC1.O>[NH2:16][C@@H:11]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]([OH:9])[C:27]([NH:29][C@@H:30]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH3:31])=[O:28]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 11202880(2S)-2-{[(benzyloxy)carbonyl]amino}-1-({[(1R)-1-phenylethyl]amino}carbonyl)hexyl benzoate

생성물 1

HCID 11265560(3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide수율 95.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

A mixture of 8.75 g (17.4 mmol) of (2S)-2-{[(benzyloxy)carbonyl]amino}-1-({[(1R)-1-phenylethyl]amino}carbonyl)hexyl benzoate and 6.97 g (174 mmol) of sodium hydroxide in 175 mL of dioxane and 75 mL of water was heated at reflux for 3 h. Upon cooling to room temperature, the reaction mixture was diluted with 100 mL of water and extracted with ethyl acetate. The combined ethyl acetate layers were dried over potassium carbonate and concentrated to afford 4.38 g (95%) of (3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.08 (d, J=8 Hz, 1H), 7.39-7.20 (m, 5H), 4.99 (m, 1H), 4.51 (br s, 1H), 3.71 (d, J=3 Hz, 1H), 2.81 (m, 1H), 1.50-1.05 (m, 9H), 0.87 (t, 3H). ES-LCMS m/z 265 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers were dried over potassium carbonate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bae9cd00dec04a909affc48fd48dcc55
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402606B2

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