Methanesulfonyl chloride → HCID 86659107, compound

HRID 1944947Notes

Reaction equation

HRID 1944947 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(C(C)C)C(C)C.[OH:15][CH2:16][C:17]1[CH:18]=[C:19]([S:23]([C:26]2[CH:27]=[C:28]3[C:33](=[C:34]([CH3:36])[CH:35]=2)[N:32]=[CH:31][C:30]([C:37]([NH2:39])=[O:38])=[C:29]3[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH3:48])[CH:42]=2)(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1>>[CH3:1][S:2]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([C:26]2[CH:27]=[C:28]3[C:33](=[C:34]([CH3:36])[CH:35]=2)[N:32]=[CH:31][C:30]([C:37](=[O:38])[NH2:39])=[C:29]3[NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH3:48])[CH:42]=2)(=[O:25])=[O:24])[CH:18]=1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 66988709HCID 66988709, compound

Product 1

HCID 86659107HCID 86659107, compoundYield 118.8%

Procedure

Methanesulfonyl chloride (0.06 mL, 1.474 mmol) and DIEA (0.243 mL, 1.394 mmol) were added to a stirring solution of Intermediate 134 (330 mg, 0.697 mmol) at rt. The reaction was monitored by LC/MS and additional methanesulfonyl chloride (0.06 mL, 1.474 mmol) and DIEA (0.243 mL, 1.394 mmol) were added after 3 h. The resulting reaction mixture was stirred for an additional 1 h then quenched with satd. NaHCO3 (50 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 (s), and concentrated to give the title compound (460 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C26H26N3O7S2+ 556.1. Found m/z=556.1 (M+H)+.

Workup

  1. additionwere added after 3 h
  2. customThe resulting reaction mixture
  3. customthen quenched with satd
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  5. washThe combined organic layers were washed with H2O (100 mL), brine (100 mL)
  6. dry with materialdried over Na2SO4 (s)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9d2647cf6da84ea78319910fdfa68fd7
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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