Sulfuric Acid → HCID 14387464, compound

HRID 1389338Notes

Reaction equation

HRID 1389338 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].S(=O)(=O)(O)O.[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([BH3-])#N.[Na+]>CO>[CH:14]1([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 6287L-ValineHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 14387464HCID 14387464, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the m-phenoxybenzyl ester of valine (2 g, 0.0067 mole) in methanol (30 ml) is added concentrated sulfuric acid to bring to about pH 6. Cyclohexanone (0.6 g, 0.006 mole) is then added followed by 3A molecular sieves and sodium cyanoborohydride (0.25 g, 0.004 mole). Additional sulfuric acid is added to keep pH at about 6. After about 24 hours, the reaction is worked up by removing methanol by rotoevaporation and the residue is poured into water and 10% sodium carbonate followed by extraction with ether. The combined ether extracts are filtered and concentrated and the product is isolated by preparatory TLC (10% ether/hexane) to yield the m-phenoxybenzyl ester of N-cyclohexylvaline.

Workup

  1. customby removing methanol by rotoevaporation
  2. additionthe residue is poured into water and 10% sodium carbonate
  3. extractionfollowed by extraction with ether
  4. filtrationThe combined ether extracts are filtered
  5. concentrationconcentrated
  6. customthe product is isolated by preparatory TLC (10% ether/hexane)

Sources & evidence

ORD record
ord-402a7d53f9f64b9a82d99028a0ab43cd
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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