L-Valine → HCID 6993292, compound

HRID 1722880Notes

Reaction equation

HRID 1722880 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.C[SH+]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.[NH2:36][C@H:37]([C:41]([OH:43])=[O:42])[CH:38]([CH3:40])[CH3:39].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:27]([O:26][C:24]([NH:23][C@H:22]([C:21]([NH:36][C@H:37]([C:41]([OH:43])=[O:42])[CH:38]([CH3:40])[CH3:39])=[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 178504122HCID 178504122, 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-methylsulfoniophenyl ester p-toluenesulfonate, and 20 ml of an aqueous solution of 0.91 g of valine and 1.1 ml of triethylamine was dropwise added thereto 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 dropwise added
  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-19ed631844774a388c6545dd575113ec
Source dataset
uspto-grants-1989_08
Patent number
US04857656

Reaction notes

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