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Hydrochloric Acid → (2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acid

HRID 1970775
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HRID 1970775 반응식
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:4].[OH-].[Na+].Cl>CO>[C:11]([NH:10][C@H:8]1[CH2:7][N:6]([C:19](=[O:29])[CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:9]1)(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
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5

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25001500Methyl (2S,4R)-4-benzamido-1-((tert-butoxycarbonyl)glycyl)pyrrolidine-2-carboxylate

생성물 1

HCID 16738323(2S,4R)-4-benzamido-1-(2-((tert-butoxycarbonyl)amino)acetyl)pyrrolidine-2-carboxylic acid수율 100.1%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
-3 °C

실험 절차

To a solution of (2S,4R) methyl-4-benzamido-1-(2-(tert-butoxycarbonyl-amino)acetyl)pyrrolidine-2-carboxylate (23.33 g, 0.0575 mol) in methanol (450 mL) was added NaOH (0.2875 mol, 144 mL of 2N aqueous solution) at −1 to 1° C. over 15 min. The mixture was stirred at −5 to −1° C. for 2.5 h. HCl (0.2875 mol, 144 mL of 2N aqueous solution) was added at −3 to 1° C. over 25 min. MeOH was distilled off under vacuum, then 500 mL of EtOAc was added. The aqueous phase was saturated with NaCl and the phases were separated. The aqueous phase was extracted with 2×250 mL EtOAc and the combined EtOAc solution was dried over MgSO4, and concentrated to afford 22.54 g of (2S,4R) 4-benzamido-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid as a white foamy solid (contains 6.6 wt % EtOAc; 94% yield adjusted to residual EtOAc). 1H NMR (CD3OD, δ, ppm): 7.87-7.79 (m, 2 H), 7.58-7.42 (m, 3 H), 4.81-4.7 (m 1 H), 4.69-4.56 (m, 1 H), 4.05-3.72 (m, 3 H), 3.67-3.49 (m, 1 H), 2.64-2.28 (m, 2 H), 1.43 (s, 9 H). MS (m/z, positive ESI) for M+H: 392; for M+Na: 414.

후처리

  1. distillationMeOH was distilled off under vacuum
  2. addition500 mL of EtOAc was added
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with 2×250 mL EtOAc
  5. dry with materialthe combined EtOAc solution was dried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-29808223636d40d98a6bb6e370a80556
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431540B2

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