1,1'-Carbonyldiimidazole → tert-butyl N-(3-(methoxy(methyl)carbamoyl)propyl)carbamate

HRID 579538Notes

Reaction equation

HRID 579538 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:28][O:29][NH:30][CH3:31]>ClCCl>[CH3:28][O:29][N:30]([CH3:31])[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acid

Product 1

HCID 23112516tert-butyl N-(3-(methoxy(methyl)carbamoyl)propyl)carbamateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While under an atmosphere of argon, a room temperature solution of 4-(tert-butoxycarbonylamino) butanoic acid (20 g, 0.098 mol) in dichloromethane (280 mL, 0.35 M) was treated with CDI (17.6 g, 0.108 mol). After 1.5 hr, O,N-dimethylhydroxylamine hydrochloride (10.6 g; 0.108 mol) was added, and the resulting solution was stirred overnight. The mixture was added to a separatory funnel, diluted with dichloromethane (220 mL) and washed successively with 2 M HCl (2×), 1 M NaOH and sat'd aq sodium chloride, dried over MgSO4, filtered and concentrated to give tert-butyl 4-(methoxy(methyl)amino)-4-oxobutylcarbamate (23.8 g, 98%). ESI MS found for C11H22N2O4 m/z [269.4 (M+Na+)].

Workup

  1. additionThe mixture was added to a separatory funnel
  2. washwashed successively with 2 M HCl (2×), 1 M NaOH
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d2b50bf178884b6d94bec3e8297efbc6
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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