HCID 67399201, compound → HCID 67396216, compound

HRID 914516Notes

Reaction equation

HRID 914516 reaction equation
[C:1]([CH2:4][C:5]1[N:6]=[C:7]([S:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[S:8][CH:9]=1)(O)=[O:2]>O1CCCC1>[OH:2][CH2:1][CH2:4][C:5]1[N:6]=[C:7]([S:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[S:8][CH:9]=1

Participants

3

Reactant 1

HCID 67399201HCID 67399201, compound

Product 1

HCID 67396216HCID 67396216, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-{[4-(carboxymethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin (10 g) synthesized in Example 461-4 in tetrahydrofuran (50 mL) was added 1 mol/L borane-tetrahydrofuran complex (25 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the reaction mixture, washed twice with tetrahydrofuran-methanol (1:1) solution, three times with tetrahydrofuran, twice with methanol, once with piperidine, once with tetrahydrofuran and once with methanol in this order, and vacuum dried. To this resin was added 1 mol/L borane-tetrahydrofuran complex (25 ml) again, and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the reaction mixture, washed once each with tetrahydrofuran, tetrahydrofuran-methanol (1:1) solution and tetrahydrofuran-piperidine (1:1) solution, then washed three times each with tetrahydrofuran and methanol, and vacuum dried to give the title pale-yellow resin (8.6 g).

Workup

  1. additionwas added 1 mol/L borane-tetrahydrofuran complex (25 ml) under ice-
  2. temperaturecooling
  3. filtrationThe resin was collected by filtration from the reaction mixture
  4. washwashed twice with tetrahydrofuran-methanol (1:1) solution, three times with tetrahydrofuran, twice with methanol, once with piperidine, once with tetrahydrofuran and once with methanol in this order, and vacuum
  5. customdried
  6. additionTo this resin was added 1 mol/L borane-tetrahydrofuran complex (25 ml) again
  7. stirringthe mixture was stirred at room temperature overnight
  8. filtrationThe resin was collected by filtration from the reaction mixture
  9. washwashed once each with tetrahydrofuran, tetrahydrofuran-methanol (1:1) solution and tetrahydrofuran-piperidine (1:1) solution
  10. washwashed three times each with tetrahydrofuran and methanol, and vacuum
  11. customdried

Sources & evidence

ORD record
ord-f3382cfbca444208806d389980276391
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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