Di-tert-butyl dicarbonate → Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

HRID 458234

반응식

HRID 458234 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[C:13]([O:17][C:18]([O:20]C(OC(C)(C)C)=O)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 90495Di-tert-butyl dicarbonateHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

생성물 1

HCID 21911455Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate수율 72%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 100 mmol), di-t-butyldicarbonate (26.2 g, 120 mmol) and 4-dimethylaminopyridine (800 mg, 6.55 mmol) in dry tetrahydrofuran (300 mL) was stirred under nitrogen for 18 h. The solvent was evaporated in vacuo. The residue was suspended in dichloromethane (1 L) and filtered through a pad of celite. The filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine, dried (MgSO4), and concentrated in vacuo. The residue was triturated with hexanes. The solid was filtered and dried in vacuo to obtain the title compound (20 g, 72%) as a tan solid.

후처리

  1. customThe solvent was evaporated in vacuo
  2. filtrationfiltered through a pad of celite
  3. washThe filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexanes
  7. filtrationThe solid was filtered
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-817822f9faf14724811ddf694abbec6a
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189854B2

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