Potassium tert-butoxide → HCID 71136946, compound

HRID 2361596Notes

Reaction equation

HRID 2361596 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]23[CH2:25][C@H:24]2[CH:23]=[CH:22][CH:21]([CH3:26])[CH2:20][CH2:19][CH2:18][C@@H:17]([CH3:27])[C@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:15](=[O:36])[N:14]2[CH2:37][C@H:38]([OH:40])[CH2:39][C@H:13]2[C:12](=[O:41])[NH:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl[C:43]1[C:52]2[C:47](=[C:48]([Cl:53])[CH:49]=[CH:50][CH:51]=2)[C:46]([O:54][CH3:55])=[CH:45][N:44]=1.CC([O-])(C)C.[K+]>CS(C)=O>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]2[C:47]=1[C:46]([O:54][CH3:55])=[CH:45][N:44]=[C:43]2[O:40][C@H:38]1[CH2:37][N:14]2[C:15](=[O:36])[C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:34])[CH3:32])[C@H:17]([CH3:27])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:26])[CH:22]=[CH:23][C@@H:24]3[CH2:25][C@@:10]3([C:8](=[O:9])[NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])[NH:11][C:12](=[O:41])[C@@H:13]2[CH2:39]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 71137309HCID 71137309, compoundHCID 71742711HCID 71742711, compound

Product 1

HCID 71136946HCID 71136946, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl ((2R,6S,7R,13aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-hydroxy-7,11-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamate (500 mg, 0.8 mmol) and 1,5-dichloro-4-methoxyisoquinoline (230 mg, 1.0 mmol) in DMSO (5 mL) was added t-BuOK (1 M solution in THF, 450 mg, 4.0 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mass was quenched with aqueous citric acid solution and extracted with ethyl acetate (150 mL×3). The combined organic layer was washed with water, brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound as diastereomer mixture. MS: MS m/z 789.3 (M++1).

Workup

  1. customThe reaction mass was quenched with aqueous citric acid solution
  2. extractionextracted with ethyl acetate (150 mL×3)
  3. washThe combined organic layer was washed with water, brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto get crude compound as diastereomer mixture

Sources & evidence

ORD record
ord-da219bb9942d4e969dc3a7c1471003e1
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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