Dimethylacetamide → HCID 25116944, compound

HRID 1640508Notes

Reaction equation

HRID 1640508 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2/[CH:13]=[CH:14]/[C:15]([NH:17][CH2:18][C@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:26]=[CH:27][C:28]3[S:33][CH2:32][C:31](=[O:34])[NH:30][C:29]=3[CH:35]=2)[CH2:20]1)=[O:16].CS(N)(=O)=[O:38].CC(N(C)C)=O.CC(O)(C)C.[OH2:52]>>[OH:52][C@@H:14]([C@H:13]([OH:38])[C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[N:4]=2)[N:9]=[CH:8][CH:7]=1)[C:15]([NH:17][CH2:18][C@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:26]=[CH:27][C:28]3[S:33][CH2:32][C:31](=[O:34])[NH:30][C:29]=3[CH:35]=2)[CH2:20]1)=[O:16]

Participants

5

Reactant 4

HCID 31374DimethylacetamideHCID 72879MethanesulfonamideHCID 66736401HCID 66736401, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 25116944HCID 25116944, compoundYield 35%

Procedure

A mixture of the compound of Example 4 (0.08 g, 0.16 mmol), methanesulfonamide (0.017 g) and AD-mix β (0.7 g) in t-BuOH/H2O (5 mL/5 mL) was vigorously stirred at rt overnight. DMA (0.5 mL) was added and stirring continued for 5 h. The reaction was carefully quenched by the portionwise addition of sodium bisulfite (1 g). The phases were separated and the aq. phase extracted with EA. The combined org. layers were dried over MgSO4 and concentrated. Chromatography on SiO2 (EA/MeOH 9:1, 4:1, +1% NH4OH) followed by trituration with ether/MeOH gave the desired product as a colourless solid (0.030 g, 35% yield).

Workup

  1. stirringstirring
  2. waitcontinued for 5 h
  3. customThe reaction was carefully quenched by the portionwise addition of sodium bisulfite (1 g)
  4. customThe phases were separated
  5. extractionthe aq. phase extracted with EA
  6. dry with materiallayers were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e21a12150e9480e8c70b918cb9397a3
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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