Methanesulfonyl chloride → 3-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

HRID 1504844Notes

Reaction equation

HRID 1504844 reaction equation
[OH:1][CH2:2][CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH:3]([NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])[CH2:4][NH:5][C:6]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:15])(=[O:27])=[O:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 755959732-(Boc-amino)-3-(Cbz-amino)-1-propanol

Product 1

HCID 867317143-{[(Benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl tert-butyl (3-hydroxypropane-1,2-diyl)biscarbamate (60.0 g, 185 mmol) in DCM (1000 mL) was added methanesulfonylchloride (23 g, 200 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 12 hours, the reaction mixture was concentrated under reduced pressure and purified directly by chromatography on silica gel to give 3-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate. MS ESI calc'd. for C17H27N2O7S [M+H]+ 403. found 403. 1H NMR (400 MHz, CD3OD) δ 7.34-7.32 (m, 5), 5.17-5.07 (m, 2H), 4.18-4.16 (m, 2H), 4.09-3.91 (m, 1H), 3.29-3.28 (m, 2H), 3.05 (s, 3H), 1.42 (s, 9H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified directly by chromatography on silica gel

Sources & evidence

ORD record
ord-ce87acb0f6984965ac41d9863995ff7e
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

Loading…