Triethylamine → HCID 86675583, compound

HRID 1422602Notes

Reaction equation

HRID 1422602 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:5][C:4]1([NH:15][C:16](=[O:19])[O:17][CH3:18])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH2:2][CH:3]1[CH2:5][C:4]1([NH:15][C:16]([O:17][CH3:18])=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 78035674HCID 78035674, compound

Product 1

HCID 86675583HCID 86675583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl (1SR,2RS)-2-(hydroxymethyl)-1-(3-nitrophenyl)cyclopropylcarbamate (intermediate B7a) (3.5 g, 13.1 mmol, Eq: 1.00) in dichloromethane (20 ml) at 0° C. was added triethylamine (2.66 g, 3.66 ml, 26.3 mmol, Eq: 2.00) followed by dropwise addition of methanesulfonyl chloride (2.26 g, 1.54 ml, 19.7 mmol, Eq: 1.50) and the mixture was stirred at 0° C. for 2 h. Poured into ice cold 1 M HCl-sol., extracted with tert-butyl methyl ether, washed organic layer with sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow oil. MS (ISP): m/z=362.1 [(M+NH4)+].

Workup

  1. extraction, extracted with tert-butyl methyl ether
  2. washwashed organic layer with sat. NaHCO3-sol
  3. dry with materialand brine, dried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a yellow oil

Sources & evidence

ORD record
ord-5c5921e0906847a6bdc45301cb297887
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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