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

HRID 340008ノート

反応式

HRID 340008 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8260b58114fa4f20be81c01867bbcf7f
出典データセット
uspto-grants-2014_11
特許番号
US08895571B2

反応ノート

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