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Sodium Hydroxide → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid

HRID 446969
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HRID 446969 반응식
C[O:2][C:3]([CH:5]1[CH2:9][N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]2[CH2:14][CH2:15][N:16]([C:17](=[O:33])[CH:18]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:6]12)=[O:4].[OH-].[Na+]>CO>[C:29]([O:28][C:26]([NH:25][CH:18]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:17]([N:16]1[CH:6]2[CH:7]([N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:9][CH:5]2[C:3]([OH:4])=[O:2])[CH2:14][CH2:15]1)=[O:33])=[O:27])([CH3:32])([CH3:30])[CH3:31]
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 672807304-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

생성물 1

HCID 672816954-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid수율 91.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 28 (1.1 g, 2.3 mmol) in MeOH (20 mL) was treated with 1M NaOH (10 mL) at ambient temperature. After 40 min, the solution was concentrated, acidified with 1M HCl until pH˜2, and extracted with EtOAc. The organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 29 (1.0 g) as a light yellow-colored foam which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ5.23 (d, J=9.0 Hz, 1H), 4.71 (d, J=6.3 Hz, 1H), 4.33-4.16 (m, 2H), 4.16-4.06 (m, 2H), 3.82-3.78 (m, 1H), 3.73-3.66 (m, 2H), 3.17 (m, 1H), 2.92 (s, 3H), 2.66 (dd, J=5.1, 13.5 Hz, 1H), 2.13 (m, 1H), 1.77-1.55 (m, 6H), 1.43 (s, 9H), 1.29-1.01 (m, 6H) ppm.

후처리

  1. concentrationthe solution was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a5e1a1da39c244c1b7566a08dbf9f43f
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481495B2

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