Methanesulfonyl chloride → N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane

HRID 1923978Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:20])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:21](Cl)([CH3:24])(=[O:23])=[O:22]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of tert-butyl N-(3-{[(tert-butoxy)carbonyl]amino}-2-hydroxypropyl)carbamate XXXIX (1.83 g, 6.3 mmol) in DCM was added TEA (1.38 mL, 10 mmol) was added. The mixture was cooled to 10° C. before adding mesyl chloride (0.77 mL, 10 mmol) dropwise. The reaction mixture was stirred for 30 min and then the solvent was removed under reduced pressure. The residue was dissolved in DCM, washed 1 M HCl (3×), 5% NaHCO3 and dried over MgSO4. The solvent was again removed under vacuum to give tert-butyl N-(3-{[(tert-butoxy)carbonyl]amino}-2-(methanesulfonyloxy)propyl)carbamate XL (2.31 g, 6.3 mmol, 99% yield). ESIMS found for C14H28N2O7S m/z 369 (M+H).

Workup

additionwas added
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved in DCM
washwashed 1 M HCl (3×), 5% NaHCO3
dry with materialdried over MgSO4
customThe solvent was again removed under vacuum

Sources & evidence

ORD record: ord-994a5c16385c4c5fa2fe8f4974c4a00a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178490B2

Reaction notes

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