Methanesulfonyl chloride → HCID 58007547, compound

HRID 1094351Notes

Reaction equation

HRID 1094351 reaction equation
Cl.[NH2:2][C@@H:3]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:4]([N:6]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([CH3:26])[CH:20]=1)[CH2:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)=[O:5].[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[CH3:26][C:21]1[CH:20]=[C:19]([N:6]([CH2:7][CH2:8][C:9]2[CH:10]=[N:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[C:4](=[O:5])[C@@H:3]([NH:2][S:34]([CH3:33])(=[O:36])=[O:35])[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:22]=1[CH3:25]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66637156HCID 66637156, compound

Product 1

HCID 58007547HCID 58007547, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-amino-N-(3,4-dimethyl-phenyl)-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide hydrochloride (40 mg, 0.086 mmol, derived from example 1) in dry CH2Cl2 (1.5 mL) was treated with methanesulphonyl chloride (10 mg, 0.087 mmol) under Argon and the mixture stirred at ambient temperature for 30 min then quenched with aqueous Na2CO3 (2 M, 1 mL), concentrated, then redissolved in EtOAc (15 mL) and washed with aqueous Na2CO3 (2 M, 3×15 mL). The combined aqueous layers were extracted with EtOAc (15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (42 mg, 96%) as a light yellow oil. MS m/e: 506.1 [M+H]+.

Workup

  1. customthen quenched with aqueous Na2CO3 (2 M, 1 mL)
  2. concentrationconcentrated
  3. dissolutionredissolved in EtOAc (15 mL)
  4. washwashed with aqueous Na2CO3 (2 M, 3×15 mL)
  5. extractionThe combined aqueous layers were extracted with EtOAc (15 mL)
  6. dry with materialthe combined organic layers dried over sodium sulfate
  7. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record
ord-56c8303466404835a3bd7d7ef5d48a13
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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