Water → 2-[(tert-Butoxycarbonyl)amino]-1-[(4-cyanophenoxy)methyl]ethyl methanesulfonate

HRID 1374095Notes

Reaction equation

HRID 1374095 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:8]1[CH:26]=[CH:25][C:11]([O:12][CH2:13][CH:14]([OH:24])[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:9]=1)#[N:7].O.C(Cl)Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:1][S:2]([O:24][CH:14]([CH2:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:26][CH:25]=1)[CH2:15][NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:23])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 21867654Tert-butyl 3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

Product 1

HCID 218675772-[(tert-Butoxycarbonyl)amino]-1-[(4-cyanophenoxy)methyl]ethyl methanesulfonateYield 103.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (22.3 g 0.195 mol) was added over the course of 1.5 hours to a cooled (0° C.) solution of tert-butyl 3-(4-cyano-phenoxy)-2-hydroxypropylcarbamate (from step (iii) above; 51.2 g, 0.177 mol) and 4-(dimethylamino)pyridine (1.3 g, 10.6 mmol) in pyridine (250 mL), kept under an inert atmosphere. The reaction mixture was stirred for 2 h at rt before water and DCM were added. The organic layer was separated, washed with water, dried (MgSO4) and concentrated in vacuo to yield 68.1 g (100%) of the sub-title compound.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2830d4f99fbe4dcab133355c23b1046e
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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