Benzyl succinimido carbonate → HCID 86705287、化合物

HRID 879231ノート

反応式

HRID 879231 の反応式
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

参加物

8

反応物 2

HCID 83172Benzyl succinimido carbonateHCID 86705285HCID 86705285、化合物

生成物 2

HCID 86705287HCID 86705287、化合物収率 28%HCID 86705288HCID 86705288、化合物収率 13%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(+/−)-Benzyl ((6R,8R,10S)-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,10S)-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.

後処理

  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

出典と根拠

ORDレコード
ord-eceac986632d41a7bb343726575e297b
出典データセット
uspto-grants-2015_03
特許番号
US08987457B2

反応ノート

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