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

HRID 416336Notes

Reaction equation

HRID 416336 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-a177f58042684e47a89beda14323d67b
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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