Triethylamine → HCID 86673867, compound

HRID 1527517Notes

Reaction equation

HRID 1527517 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[F:18])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[F:18])[CH2:9][O:10][S:27]([CH3:30])(=[O:29])=[O:28])=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68283916HCID 68283916, compound

Product 1

HCID 86673867HCID 86673867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [(S)-1-(3-chloro-2-fluoro-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (550 mg, 1.9 mmol) and triethylamine (0.29 mL, 2.09 mmol) in CH2Cl2 (5.5 mL) cooled at −10° C. was added under nitrogen atmosphere mesylchloride (0.16 mL, 2.09 mmol) and the reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with ice and water then extracted twice with EtOAc. The combined organic layers were washed with water, dried (Na2SO4), filtered and concentrated. The crude material was used without purification in the next step. MS (UPLC/MS): 412.3/414.3 [M+HCOO]−; tR (HPLC conditions a): 3.66 min.

Workup

  1. customThe reaction mixture was quenched with ice and water
  2. extractionthen extracted twice with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was used without purification in the next step
  8. custom3.66 min.

Sources & evidence

ORD record
ord-78fbc91c09af467599b8f4109ee93ab2
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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