Water → HCID 71666068, compound

HRID 624675Notes

Reaction equation

HRID 624675 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([C:24]2[S:46][C:27]3=[N:28][C:29]([N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]4)=[CH:30][C:31](=[O:32])[N:26]3[N:25]=2)[CH:16]=[C:17]([C:19]([OH:23])(C)[CH2:20]O)[CH:18]=1)=[O:11])=O)(C)(C)C.O>C1COCC1>[C:19]([C:17]1[CH:18]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][NH2:8])[CH:14]=[C:15]([C:24]2[S:46][C:27]3=[N:28][C:29]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[CH:30][C:31](=[O:32])[N:26]3[N:25]=2)[CH:16]=1)(=[O:23])[CH3:20]

Participants

4

Reactant 2

HCID 962WaterHCID 89711402HCID 89711402, compound

Product 1

HCID 71666068HCID 71666068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(2-(3-(2-(tert-butoxycarbonylamino)-acetamido)-5-(1,2-dihydroxypropan-2-yl)phenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (27.0 mg, 0.041 mmol) in THF (0.5 ml)/Water (0.500 ml) is added NaIO4 (17.5 mg, 0.082 mmol). The mixture is stirred at room temperature for 2 h and then extracted with EtOAc (2×10 ml). The combined organic layers are washed with brine and dried over Na2SO4. After the removal of organic solvent in vacuo, the crude product (26 mg) is directly used without further purification for the next step as described in Step 6 of Example 1.

Workup

  1. extractionextracted with EtOAc (2×10 ml)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter the removal of organic solvent in vacuo
  5. customthe crude product (26 mg) is directly used without further purification for the next step

Sources & evidence

ORD record
ord-decd6f6bbf0d4e7ba72916cffd8ecf65
Source dataset
uspto-grants-2016_04
Patent number
US09303044B2

Reaction notes

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