Lithium Hydroxide → HCID 86653392, compound

HRID 1915964Notes

Reaction equation

HRID 1915964 reaction equation
[C:1]([O:5][C:6](=[O:78])[CH2:7][CH2:8][C@H:9]([C:40](=[O:77])[NH:41][C@@H:42]([C:64](=[O:76])[NH:65][C:66]1([CH:69]([OH:75])[CH2:70][C:71]([O:73]C)=[O:72])[CH2:68][CH2:67]1)[CH2:43][S:44][C:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[NH:10][C:11](=[O:39])[CH2:12][C@H:13]([OH:38])/[CH:14]=[CH:15]/[CH2:16][CH2:17][S:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.O>[C:1]([O:5][C:6](=[O:78])[CH2:7][CH2:8][C@H:9]([C:40](=[O:77])[NH:41][C@@H:42]([C:64](=[O:76])[NH:65][C:66]1([CH:69]([OH:75])[CH2:70][C:71]([OH:73])=[O:72])[CH2:67][CH2:68]1)[CH2:43][S:44][C:45]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)([C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[NH:10][C:11](=[O:39])[CH2:12][C@H:13]([OH:38])/[CH:14]=[CH:15]/[CH2:16][CH2:17][S:18][C:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86653393HCID 86653393, compound

Product 1

HCID 86653392HCID 86653392, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 7 (927.1 mg, 0.850 mmol) in THF (12 mL) at 0° C. was added LiOH (30.6 mg, 1.28 mmol) in water (3 mL) and the reaction mixture was stirred for 3.25 h. The mixture was then quenched with 1M HCl (aq) (20 mL), diluted with water (20 mL), and treated with EtOAc (60 mL). The layers were separated, and the product was extracted with EtOAc (3×60 mL). The organic layers were combined, washed with saturated brine (50 mL), dried (MgSO4), and concentrated in vacuo to give the product 8 (789.1 mg, 86%) as a white solid (diastereoisomers 1:1 ratio). Compound 8 was used in the next step further purification [MS (ES+) 1097.4 (100%, [M+Na]+)].

Workup

  1. customThe mixture was then quenched with 1M HCl (aq) (20 mL)
  2. additiondiluted with water (20 mL)
  3. additiontreated with EtOAc (60 mL)
  4. customThe layers were separated
  5. extractionthe product was extracted with EtOAc (3×60 mL)
  6. washwashed with saturated brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-114fc3abbca44781b9c927615f714624
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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