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

HRID 1425909Notes

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 XXVI (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% aq. 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 XXVII (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% aq. NaHCO3
dry with materialdried over MgSO4
customThe solvent was again removed under vacuum

Sources & evidence

ORD record: ord-fb675161f0314cf8934e9abf86f0e0ab
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933018B2

Reaction notes

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