(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid → (S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate

HRID 340008노트

반응식

HRID 340008 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH:14]1[CH2:15][CH2:16]1)([CH3:2])([CH3:4])[CH3:3]

참가 물질

3

반응물 1

HCID 5706350(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

생성물 1

HCID 59227079(S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-cyclopropylpropanoic acid (2.5 g, 11 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 1.0 M borane-THF complex in THF (32.4 mL). After addition, the reaction mixture was stirred at room temperature for 3 hours, then cooled down with an ice-bath, quenched by the slow addition of AcOH:MeOH (1:5, 20 mL) and the mixture was then warmed to room temperature for 2 hours. The THF volume was reduced by ½ and the product was partitioned between saturated aqueous NaHCO3 and DCM. The combined organic fractions were dried over Na2SO4 and concentrated under reduced pressure to give an oil residue, which was used directly in the next reaction without further purification. LC-MS found: 216.1 (M+H)+.

후처리

  1. additionAfter addition
  2. temperaturecooled down with an ice-bath
  3. customquenched by the slow addition of AcOH:MeOH (1:5, 20 mL)
  4. temperaturethe mixture was then warmed to room temperature for 2 hours
  5. customthe product was partitioned between saturated aqueous NaHCO3 and DCM
  6. dry with materialThe combined organic fractions were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil residue, which
  9. customwas used directly in the next reaction without further purification

출처 및 근거

ORD 기록
ord-8260b58114fa4f20be81c01867bbcf7f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895571B2

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