Methanesulfonyl chloride → (1R)-2-{[(Benzyloxy)carbonyl]amino}-1-[(4-cyanophenoxy)methyl]ethyl Methanesulfonate

HRID 411542Notes

Reaction equation

[C:1]([C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][C@H:9]([OH:22])[CH2:10][NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1)#[N:2].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:25][S:26]([O:22][C@@H:9]([CH2:8][O:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:24][CH:23]=1)[CH2:10][NH:11][C:12]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:21])(=[O:28])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(Dimethylamino)pyridine (0.22 g, 1.77 mmol) was added to a solution of benzyl (2R)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate (see step (iii) above; 5.79 g, 17.7 mmol) in pyridine (15 mL). The mixture was cooled to 0° C., and methanesulfonyl chloride (2.23 g, 19.5 mmol) was added slowly at 0° C. The mixture was allowed to reach rt, at which temperature it was then stirred for 4 h. The solvent was evaporated. DCM (100 mL) was added, washed with water, 1 N H2SO4 and brine, dried (Na2SO4) and evaporated giving 6.0 g (84%) of a yellow oil.

Workup

customto reach rt, at which temperature it
customThe solvent was evaporated
additionDCM (100 mL) was added
washwashed with water, 1 N H2SO4 and brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-1e21f0f4818643ee9b5405d830891651
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559162B2

Reaction notes

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