Benzyl succinimido carbonate → HCID 86705287, 화합물

HRID 705316노트

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HRID 705316 반응식
C(OC([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@@H:18]1[CH2:27][C@H:26]([CH3:28])[C:21]2([O:25][CH2:24][CH2:23][O:22]2)[C@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:19]1)=O)C1C=CC=CC=1.C(ON1C(=O)CCC1=O)(OCC1C=CC=CC=1)=O>CO.C(Cl)Cl.CCOC(C)=O.[Pd]>[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@H:18]1[CH2:27][C@@H:26]([CH3:28])[C:21]2([O:22][CH2:23][CH2:24][O:25]2)[C@@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:19]1.[NH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C@@H:18]1[CH2:27][C@H:26]([CH3:28])[C:21]2([O:22][CH2:23][CH2:24][O:25]2)[C@H:20]([NH:29][C:30](=[O:39])[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:19]1

참가 물질

8

반응물 2

HCID 83172Benzyl succinimido carbonateHCID 86705285HCID 86705285, 화합물

생성물 2

HCID 86705287HCID 86705287, 화합물수율 28%HCID 86705288HCID 86705288, 화합물수율 13%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

(+/−)-Benzyl ((6R,8R,10 S)-8-(3-((benzoxycarbonyl)amino)pyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-yl)carbamate (1.0 equiv.) was dissolved in MeOH (0.10 M) and degassed with Argon to vacuum. Pd/C (0.05 equiv.) was added and the mixture was stirred under a H2 balloon for 20 hrs. The mixture was filtered and concentrated. The crude and CBZ-OSu (0.99 equiv.) were dissolved in DCM (0.20 M). The reaction was stirred at room temperature for 2 hrs. The solution was diluted with EtOAc and washed with water, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by ISCO chromatography. Purification was completed via SFC (40% EtOH, 15 mL/min, OJ column) to yield benzyl (6S,8S,10R)-8-(3-aminopyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-ylcarbamate (28% yield, 99% ee) and benzyl (6R,8R,10 S)-8-(3-aminopyridin-4-yl)-10-methyl-1,4-dioxaspiro[4.5]decan-6-ylcarbamate (13% yield, 99% ee). LC/MS (m/z)=398.2 (MH+), Rt=0.64 min.

후처리

  1. customdegassed with Argon to vacuum
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. stirringThe reaction was stirred at room temperature for 2 hrs
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by ISCO chromatography
  10. customPurification

출처 및 근거

ORD 기록
ord-4a5d6b282cc649c3aa0ee463f0538525
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173883B2

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