Methanesulfonyl chloride → HCID 86731704, compound

HRID 1504824Notes

Reaction equation

HRID 1504824 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][OH:7])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:7][CH2:6][CH:5]([NH:8][C:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:15])[CH2:4][O:3][CH2:1][CH3:2])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 75089283Carbamic acid, N-[2-ethoxy-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 86731704HCID 86731704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (1-ethoxy-3-hydroxypropan-2-yl)carbamate (2.2 g, 9.4 mmol) in DCM (40 mL) was added methanesulfonylchloride (2.10 g, 18.8 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 12 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified via chromatography on silica gel to afford 2-[(tert-butoxycarbonyl)amino]-3-ethoxypropyl methanesulfonate. MS ESI calc'd. for C11H24NO6S [M+H]+ 298. found 298. 1H NMR (400 MHz, CDCl3) δ 4.95 (s, 1H), 4.28 (d, J=8.0 Hz, 1H), 4.13-4.11 (m, 1H), 3.58-3.48 (m, 5H), 3.03 (s, 3H), 1.45 (s, 9H), 1.18 (t, J=6.8 Hz, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified via chromatography on silica gel

Sources & evidence

ORD record
ord-ef680de5d5d0468c9575847a2f2e194b
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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