Sodium Hydroxide → (2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

HRID 2275485ノート

反応式

HRID 2275485 の反応式
[NH2:1][C@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O>CC#N.O>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@@H:2]([NH:1][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 671215(R)-2-amino-3-(4-bromophenyl)propionic acid

生成物 1

HCID 7020327(2R)-3-(4-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid収率 93.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of (R)-2-amino-3-(4-bromophenyl)propionic acid (50 g, 0.2 mol) in MeCN (700 mL) was added a solution of NaOH (16.4 g, 0.4 mol) in water (700 mL) at −5° C. After stirring for 10 minutes, a solution of (BOC)2O (44.7 g, 0.2 mol) in MeCN (100 mL) was added. The mixture was warmed to room temperature and stirred overnight. After evaporation of the MeCN, the residue was diluted with DCM (800 mL) and acidified with 1 M HCl to pH 2 at −5° C. The aqueous layer was extracted with DCM (3×200 mL). The combined organic layers were washed with saturated aqueous NaCl (500 mL), dried over anhydrous Na2SO4 and concentrated to yield the title compound as a white solid (64.2 g). LC-MS: [M+Na]:366, [2M+Na]:709.

後処理

  1. stirringstirred overnight
  2. customAfter evaporation of the MeCN
  3. additionthe residue was diluted with DCM (800 mL)
  4. customacidified with 1 M HCl to pH 2 at −5° C
  5. extractionThe aqueous layer was extracted with DCM (3×200 mL)
  6. washThe combined organic layers were washed with saturated aqueous NaCl (500 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3cc11813e2f14b62a71f621f6df96c6d
出典データセット
uspto-grants-2015_09
特許番号
US09126956B2

反応ノート

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