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

HRID 1881340ノート

反応式

HRID 1881340 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-ceefe33eeb8544f98d0026339843a731
出典データセット
uspto-grants-2012_11
特許番号
US08318791B2

反応ノート

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