Pyruvic Acid → HCID 54193016, compound

HRID 34528Notes

Reaction equation

HRID 34528 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][C@@H:14]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[NH:13]1.CN1CCOCC1.C1(N=C=NC2CCCCC2)CCCCC1.[C:54](O)(=[O:58])[C:55]([CH3:57])=[O:56]>C(Cl)(Cl)Cl>[C:54]([N:13]1[C@H:14]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12]1)(=[O:58])[C:55]([CH3:57])=[O:56]

Participants

6

Reactant 4

HCID 1060Pyruvic AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 1276675077497-97-3

Product 1

HCID 54193016HCID 54193016, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

13.17 g of benzyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate tosylate (N. Yoneda, et al., Chem.Pharm.Bull., 31, 312 (1983)) was suspended in 30 mL CHCl3. N-methylmorpholine was added until the pH was 7, 6.8 g of dicyclohexylcarbodiimide and 3.17 g of pyruvic acid was added at -5° C. The reaction mixture was stirred at -50° C. for one hour and 0° C. for 48 hours. The reaction mixture was filtered, and the filtrate was concentrated to dryness to give a semi-solid, which was purified by passing through a silica gel column and eluting with ethyl acetate:hexane (1:1) to give benzyl N-pyruvoyl-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate as a yellow oil, [α]D25 -10.3°.

Workup

  1. additionwas added at -5° C
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give a semi-solid, which
  5. customwas purified
  6. washeluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-f694b268f00f48ab9a3b4eff7aa09f08
Source dataset
uspto-grants-1988_08
Patent number
US04762821

Reaction notes

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