L-Valine → HCID 6993292, compound

HRID 1586896Notes

Reaction equation

HRID 1586896 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.C[S+](C)C1C=CC(O[C:21](=[O:35])[C@H:22]([CH3:34])[NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])=CC=1.[NH2:37][C@H:38]([C:42]([OH:44])=[O:43])[CH:39]([CH3:41])[CH3:40].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:27]([O:26][C:24]([NH:23][C@H:22]([C:21]([NH:37][C@H:38]([C:42]([OH:44])=[O:43])[CH:39]([CH3:41])[CH3:40])=[O:35])[CH3:34])=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6287L-ValineHCID 8471TriethylamineHCID 88483167HCID 88483167, compound

Product 1

HCID 6993292HCID 6993292, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 50 ml of chloroform was dissolved 4.14 g of benzyloxycarbonylalanine p-dimethylsulfoniophenyl ester p-toluenesulfonate, and 20 ml of an aqueous solution of 0.91 g of valine and 1.1 ml of triethylamine was added dropwise thereto while under stirring at room temperature. The reaction mixture was stirred for 8 hours at room temperature and then separated. The chloroform layer was washed with water, dried, and concentrated under reduced pressure, and ether was added to the residue to afford white crystals.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 8 hours at room temperature
  3. customseparated
  4. washThe chloroform layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure, and ether
  7. additionwas added to the residue
  8. customto afford white crystals

Sources & evidence

ORD record
ord-77c6cf5993da41c580cfa5995d678f04
Source dataset
uspto-grants-1993_06
Patent number
US05216125

Reaction notes

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