Water → HCID 178451078, compound

HRID 1035736Notes

Reaction equation

HRID 1035736 reaction equation
[O:1]=[C:2]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:3][CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[O:12])=[N:7][N:6]=1.[BH4-].[Na+].CN(C=O)C.O>CO>[OH:1][CH:2]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:3][CH2:4][C:5]1[S:9][C:8]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C@H:19]3[CH2:20][CH2:21][C@H:22]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[O:12])=[N:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 4311764Sodium borohydride2×HCID 178451077HCID 178451077, compound

Product 1

HCID 178451078HCID 178451078, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.159 g of tert-butyl trans-(4-{4-[5-(3-oxo-3-phenylpropyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate (0.3 mmol, 1 eq.) is placed in 5 mL of methanol with stirring. The reaction medium is cooled on an ice bath and 0.012 g of sodium borohydride (0.33 mmol, 1.1 eq.) is added. 3 mL of DMF are added. After stirring for 16 hours, the reaction medium is cooled on an ice bath and 0.023 g of sodium borohydride (0.6 mmol, 2 eq.) and 3 mL of DMF are added. After stirring for 2 hours, the reaction medium is poured into water and extracted twice with ethyl acetate. The organic phase is washed three times with water, dried over magnesium sulfate and evaporated to give 0.146 g of tert-butyl trans-(4-{4-[5-(3-hydroxy-3-phenylpropyl)-[1.3.4]thiadiazol-2-ylcarbamoyl]phenyl}cyclohexyl)acetate,

Workup

  1. temperatureThe reaction medium is cooled on an ice bath
  2. stirringAfter stirring for 16 hours
  3. temperaturethe reaction medium is cooled on an ice bath
  4. stirringAfter stirring for 2 hours
  5. extractionextracted twice with ethyl acetate
  6. washThe organic phase is washed three times with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-7a1bb724c04446b3b2b64b44e5dd5de5
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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