Sodium Carbonate → HCID 67277658, compound

HRID 519314Notes

Reaction equation

HRID 519314 reaction equation
[CH2:1]([N:8]1[C@H:13]([C:14](OCC)=[O:15])[CH2:12][N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:10][C@@H:9]1[C:28](OCC)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH:13]([CH2:14][OH:15])[CH2:12][N:11]([S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:21])=[O:20])[CH2:10][CH:9]1[CH2:28][OH:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 58946770HCID 58946770, compound

Product 1

HCID 67277658HCID 67277658, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 M solution of LiAIH4 in THF (70 ml; 70 mmol) was added dropwise under cooling and stirring to 112c (10.7 g; 23.2 mmol) in THF (275 ml). The reaction mixture was refluxed for 20 min, poured on a saturated solution of Na2CO3 and extracted with TBME three times. The combined organic phases were dried over Na2SO4 and evaporated to dryness to yield a colorless solid, which was washed with TBME to yield 112d as white crystals (7 g, 80%). MS: [M+H]+: 377

Workup

  1. temperatureunder cooling
  2. temperatureThe reaction mixture was refluxed for 20 min
  3. extractionextracted with TBME three times
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated to dryness
  6. customto yield a colorless solid, which
  7. washwas washed with TBME

Sources & evidence

ORD record
ord-11cf3f90aef3469ab2debda19d39bf37
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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