L-Lactic Acid → HCID 86759847, compound

HRID 618437Notes

Reaction equation

HRID 618437 reaction equation
C(OC([NH:11][C@H:12]([B:20]([OH:22])[OH:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[C:23]([OH:28])(=[O:27])[C@H:24]([CH3:26])[OH:25]>C1C=CC=CC=1>[C:23]([O-:28])(=[O:27])[C@H:24]([CH3:26])[OH:25].[NH2:11][C@H:12]([B:20]([O-:22])[O-:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 107689L-Lactic AcidHCID 53705858HCID 53705858, compound

Product 1

HCID 86759847HCID 86759847, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.42 (5 mmol) of (R)-1-benzyloxycarbonylamino-2-phenylethane boronic acid (V) is refluxed with 80 ml of benzene and 0.45 g (5 mmol) of (S)-(+)-lactic acid (VI) in a Dean Stark apparatus for 5 hrs. After cooling the mixture is concentrated, redissolved in 75 ml of methanol and then transferred to a two-necked flask. The mixture is flushed with nitrogen, 1 gram of 10% palladium on activated carbon is added and hydrogen gas is passed through the stirred mixture for 2 hrs. 75 ml of methanol-water (1:1 v /v) is added and the mixture filtered slowly through celite (30 g). The filtrate is collected and concentrated to give (S)-lactate-1-(R)-amino-2-phenylethane boronate (VIII).

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationis concentrated
  3. dissolutionredissolved in 75 ml of methanol
  4. customtransferred to a two-necked flask
  5. customThe mixture is flushed with nitrogen, 1 gram of 10% palladium on activated carbon
  6. additionis added
  7. addition75 ml of methanol-water (1:1 v /v) is added
  8. filtrationthe mixture filtered slowly through celite (30 g)
  9. customThe filtrate is collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-31a0a1d9b66a4bd28109d762b12ae4d1
Source dataset
uspto-grants-1999_09
Patent number
US05952462

Reaction notes

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