2,6-Di-tert-butyl-4-methylpyridine → (S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

HRID 2104203ノート

反応式

HRID 2104203 の反応式
[CH2:1]([O:8][C:9]([CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.F[B-](F)(F)F.C[O+](C)C>ClCCl>[CH2:1]([O:8][C:9]([CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:13][O:14][CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

生成物 1

HCID 57976545(S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To tert-butyl (S)-1-((benzyloxy)carbonyl)-3-hydroxypropan-2-ylcarbamate (1 eq.) in dichloromethane was added 2,6-di-t-butyl 4-methylpyridine (2.5 eq.) and trimethyloxonium tetrafluoroborate (1.25 eq.) at 0° C. The reaction mixture was gradually warm to room temperature and stirred overnight. The reaction mixture was diluted with dichloromethane and washed with cold satd. sodium bicarbonate, water, and brine and dried over sodium sulfate. Purification by silica gel chromatography (25% EtOAc/Hexane) provide pure product as a colorless viscous liquid.

後処理

  1. washwashed with cold satd
  2. dry with materialsodium bicarbonate, water, and brine and dried over sodium sulfate
  3. customPurification by silica gel chromatography (25% EtOAc/Hexane)
  4. customprovide pure product as a colorless viscous liquid

出典と根拠

ORDレコード
ord-f370348922ca4d1da77958c5dd1a6921
出典データセット
uspto-grants-2009_08
特許番号
US07576221B2

反応ノート

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