Methyl vinyl sulfone → HCID 76317949, compound

HRID 522421Notes

Reaction equation

HRID 522421 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:64][CH2:63]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:41][CH2:40][NH2+:39][CH2:38][CH2:37]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.[CH:79]([S:81]([CH3:84])(=[O:83])=[O:82])=[CH2:80]>C(Cl)Cl>[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50]([NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:63][CH2:64]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])=[O:67])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:37][CH2:38][N:39]([CH2:80][CH2:79][S:81]([CH3:84])(=[O:83])=[O:82])[CH2:40][CH2:41]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 19354Methyl vinyl sulfoneHCID 81531DiisopropylethylamineHCID 117598881HCID 117598881, compound

Product 1

HCID 76317949HCID 76317949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step 1, Example 236 (50 mg, 0.057 mmol) in CH2Cl2 (3 ml) was added DIPEA (0.030 ml, 0.171 mmol) followed by methyl vinyl sulfone (12.10 mg, 0.114 mmol). The reaction was stirred in a sealed vial for 16 h at which stage LCMS indicated complete conversion to one peak corresponding to a product with desired mass. After removing the solvent the crude mixture was purified by PTLC (5% MeOH in CH2Cl2) and then repurified by PTLC using 40% acetone in hexane to furnish the title compound. LRMS m/z 981.6 (M+H)+.

Workup

  1. customAfter removing the solvent the crude mixture
  2. customwas purified by PTLC (5% MeOH in CH2Cl2)
  3. customrepurified by PTLC

Sources & evidence

ORD record
ord-d83ff7ca3e91405aad2ad06284845fba
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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