Methanesulfonyl chloride → HCID 68451927, compound

HRID 2104443Notes

Reaction equation

HRID 2104443 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[N:11]=[C:12]([C:14]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]3[NH:23][C:24]([C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=4)=[O:25])=[O:15])[S:13][C:7]=2[CH2:6]1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>N1C=CC=CC=1.Cl>[ClH:35].[Cl:35][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([C:24]([NH:23][C@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]1[NH:16][C:14]([C:12]1[S:13][C:7]3[CH2:6][N:5]([CH2:4][CH2:3][NH:2][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:10][CH2:9][C:8]=3[N:11]=1)=[O:15])=[O:25])=[CH:34]2

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67056679HCID 67056679, compound

Product 1

HCID 68451927HCID 68451927, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

The compound (110 mg) obtained in Example 40 was dissolved in pyridine (3 mL), methanesulfonyl chloride (30 μl) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. To the residue, a 85:15 mixture of methylene chloride and methanol, and water were added for partitioning the mixture. The resultant organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a pale yellow foamy substance. This product was suspended in 1N hydrochloric acid (0.3 mL), and the suspension was concentrated under reduced pressure to give the title compound (63 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue, a 85:15 mixture of methylene chloride and methanol, and water
  3. additionwere added
  4. customfor partitioning the mixture
  5. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3)
  8. customto give a pale yellow foamy substance
  9. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fbd04d7bba6443549eed67345163a9d7
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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