1,1'-Carbonyldiimidazole → (S)-2-(tert-butoxycarbonyl(methyl)amino)-6-methoxy-6-oxohexyl 1H-imidazole-1-carboxylate

HRID 340906Notes

Reaction equation

HRID 340906 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:19])[C@H:9]([CH2:17][OH:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:20]1[N:24]=[CH:23][N:22]([C:25](N2C=NC=C2)=[O:26])[CH:21]=1>C(Cl)Cl>[N:22]1([C:25]([O:18][CH2:17][C@@H:9]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:19])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:26])[CH:21]=[CH:20][N:24]=[CH:23]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57947872(S)-methyl 5-(tert-butoxycarbonyl(methyl)amino)-6-hydroxyhexanoate

Product 1

HCID 57947517(S)-2-(tert-butoxycarbonyl(methyl)amino)-6-methoxy-6-oxohexyl 1H-imidazole-1-carboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 5-(tert-butoxycarbonyl(methyl)amino)-6-hydroxyhexanoate (4.4 g, 16 mmol) in DCM (50 mL) was added CDI (3.1 g, 19 mmol). The reaction was complete in 30 min. DCM was removed. The residue was purified on silica gel column (hexanes/EtOAc 1:1) to give (S)-2-(tert-butoxycarbonyl(methyl)amino)-6-methoxy-6-oxohexyl 1H-imidazole-1-carboxylate (5.1 g, 85%) as a colorless oil. LRMS (M+Na+) m/z 392.1

Workup

  1. customDCM was removed
  2. customThe residue was purified on silica gel column (hexanes/EtOAc 1:1)

Sources & evidence

ORD record
ord-ffafdd85220a4cb296a16050510a748f
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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