Methanesulfonyl chloride → HCID 86600479, compound

HRID 851938Notes

Reaction equation

HRID 851938 reaction equation
[OH:1][CH2:2][CH:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7]2[CH:20]=[CH:21][CH:22]=[CH:23][C:6]=2[CH2:5][CH2:4]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCN(C(C)C)C(C)C>C1COCC1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:8]2[C:9](=[O:10])[CH:3]([CH2:2][O:1][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:4][CH2:5][C:6]3[CH:23]=[CH:22][CH:21]=[CH:20][C:7]2=3)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69006818HCID 69006818, compound

Product 1

HCID 86600479HCID 86600479, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxymethyl-1-(4-methoxy-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (0.26 mmol) in 2 mL of anhydrous THF at 0° C. is added MsCl (0.39 mmol) and DIEA (0.47 mmol). After the addition, the mixture is allowed to warm up to room temperature and then stirred for 1 hour. The solvent is removed under vacuum and the residue is treated with water (5 mL) and extracted with EtOAc (3×5 mL). The combined organic layers are concentrated and the residue is purified by flash column chromatography (silica gel) to provide methanesulfonic acid 1-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylmethyl ester as white crystals. Yield: 90%. MS: (ES+): 390[M+1].

Workup

  1. additionAfter the addition
  2. customThe solvent is removed under vacuum
  3. additionthe residue is treated with water (5 mL)
  4. extractionextracted with EtOAc (3×5 mL)
  5. concentrationThe combined organic layers are concentrated
  6. customthe residue is purified by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-674df8365cc64b659c90161ca1c1d99b
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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