Lithium Hydroxide → HCID 59552562, compound

HRID 1803820Notes

Reaction equation

HRID 1803820 reaction equation
[S:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([N:24]([CH2:36][C:37]([O:39]CC)=[O:38])[CH2:25][C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)=[O:23])[CH:20]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:4])(=[O:3])[NH2:2].[Li+].[OH-]>C1COCC1.O>[S:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]([N:24]([CH2:36][C:37]([OH:39])=[O:38])[CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:30][CH:31]=4)=[O:23])[CH:20]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])(=[O:4])[NH2:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59552561HCID 59552561, compound

Product 1

HCID 59552562HCID 59552562, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a 20 mL round bottomed flask equipped with a magnetic stir bar containing THF:H2O (1:1, 10 mL) was placed 139 (176 mg, 0.29 mmol). To this solution LiOH (61 mg, 1.45 mmol) was added and the reaction was allowed to stir at RT for 3 h. After the reaction was done, THF was removed and the aqueous layer was acidified to pH=3 with 6 M HCl. The reaction was then poured into brine (50 mL) and extracted into CHCl3 (3×20 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4 and concentrated in vacuo to afford BD336 (yield not determined) as a colorless solid.

Workup

  1. customTo a 20 mL round bottomed flask equipped with a magnetic stir bar
  2. customTHF was removed
  3. additionThe reaction was then poured into brine (50 mL)
  4. extractionextracted into CHCl3 (3×20 mL)
  5. washThe combined organic extracts were washed with water (20 mL), brine (20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto afford BD336 (
  9. customyield not

Sources & evidence

ORD record
ord-8ac207f3a50545f6a116d4089f94f78f
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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