Hydrochloric Acid → (R)-2-(1-hydroxy-3-phenylpropan-2-ylamino)-2-oxoacetic acid

HRID 58569

반응식

HRID 58569 반응식
C(N(CC)CC)C.[NH2:8][C@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11].Cl[C:20](=[O:26])[C:21]([O:23]CC)=[O:22].[OH-].[Na+].Cl>ClCCl.O>[OH:11][CH2:10][C@H:9]([NH:8][C:20](=[O:26])[C:21]([OH:23])=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20884Ethoxalyl chlorideHCID 853475phenylalaninol, (R)-

생성물 1

HCID 66831884(R)-2-(1-hydroxy-3-phenylpropan-2-ylamino)-2-oxoacetic acid수율 91%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매2회

실험 절차

Triethylamine (0.703 mL; 5.01 mmol) was added to the mixture of (R)-2-amino-3-phenylpropan-1-ol (0.515 g; 3.34 mmol) and ethyl 2-chloro-2-oxoacetate (0.400 mL; 3.50 mmol) in dichloromethane (15 mL) at 0° C. After addition, the mixture was stirred at room temperature for 30 minutes, diluted with 40 mL of dichloromethane and washed successively with an aqueous solution of sodium carbonate and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Water (5 mL) and a 2M solution of sodium hydroxide (5 mL; 10 mmol) were added to the resulting residue and the mixture was stirred at room temperature for 10 minutes. Water (10 mL) was added and the pH of the solution was adjusted to 1 by addition of a 6N hydrochloric acid. The formed precipitate was filtered off, and the filtrate was extracted with ethyl acetate (5×20 mL). The combined organic layers were dried over magnesium sulfate and evaporated to dryness to give 0.671 g (91%) of (R)-2-(1-hydroxy-3-phenylpropan-2-ylamino)-2-oxoacetic acid as a white solid.

후처리

  1. additionAfter addition
  2. washwashed successively with an aqueous solution of sodium carbonate and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. stirringthe mixture was stirred at room temperature for 10 minutes
  6. filtrationThe formed precipitate was filtered off
  7. extractionthe filtrate was extracted with ethyl acetate (5×20 mL)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-24cbae80b894483981edd04cd2aeb457
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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