Hydrochloric Acid → HCID 86755071, compound

HRID 849745Notes

Reaction equation

HRID 849745 reaction equation
[C:1]([O:5][C:6](=[O:38])[CH:7]([CH2:36][NH2:37])[C@H:8]([C:13](=[O:35])[NH:14][C@H:15]1[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:34])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C([N:41](CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48].Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:38])[CH:7]([CH2:36][NH:37][NH:41][S:47]([CH3:46])(=[O:49])=[O:48])[C@H:8]([C:13](=[O:35])[NH:14][C@H:15]1[CH2:32][C:31]2=[CH:33][N:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=32)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:34])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57039868HCID 57039868, compound

Product 1

HCID 86755071HCID 86755071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3R,10S)-2-(aminomethyl)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo [10.6.1.013,18 ]nonadeca-12 (19),13 (18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester (363 mg) and triethylamine (0.54 ml) in dry methylene chloride (20 ml) at 0° C. was added methanesulfonyl chloride (77 μml). The resulting mixture was stirred for 2 hours, allowing the mixture to rise to ambient temperature, then methylene chloride (100 ml) and 0.5N hydrochloric acid (50 ml) added, stirring vigorously. The aqueous layer was further extracted with methylene chloride (2×75 ml), then the combined organic layers washed with brine (100 ml). After drying the organic layer over MgSO4, it was filtered and evaporated to dryness. Purification of the residue by flash column chromatography (20-30% ethyl acetate/methylene chloride) gave (3R,10S)-2-(methylsulfonamidoaminomethyl)-5-methyl-3-(9-oxo-1,8-diaza-tricyclo[10.6.1.013,18 ]nonadeca-12(19),13(18),14,16-tetraen-10-ylcarbamoyl)hexanoic acid t-butyl ester as a white solid (211 mg).

Workup

  1. customto rise to ambient temperature
  2. stirringstirring vigorously
  3. extractionThe aqueous layer was further extracted with methylene chloride (2×75 ml)
  4. washthe combined organic layers washed with brine (100 ml)
  5. dry with materialAfter drying the organic layer over MgSO4, it
  6. filtrationwas filtered
  7. customevaporated to dryness
  8. customPurification of the residue by flash column chromatography (20-30% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-3c1b3d5610c0487ebead7e257c56c46e
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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