Phosphoric Acid → HCID 88265334, compound

HRID 1952962Notes

Reaction equation

HRID 1952962 reaction equation
[NH2:1][C@@H:2]([C:5]([NH2:7])=[O:6])[CH2:3][OH:4].[CH3:8][CH2:9][CH2:10][C:11](=O)[CH2:12][CH2:13][CH3:14].Cl.CO.C([BH3-])#N.[Na+].[P:23](=[O:27])([OH:26])([OH:25])[OH:24]>CO>[P:23]([OH:27])([OH:26])([OH:25])=[O:24].[CH3:8][CH2:9][CH2:10][CH:11]([NH:1][C@H:2]([CH2:3][OH:4])[C:5]([NH2:7])=[O:6])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 5

HCID 1004Phosphoric AcidHCID 312464-HeptanoneHCID 447822D-serine amideHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol2×

Product 1

HCID 88265334HCID 88265334, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of D-serinamide (0.01 moles, 1 g) and 4-heptanone (0.01 moles, 1.1 g) in methanol (50 ml) is added with 4M methanol HCl (0.0033 moles, 0.85 ml) and sodium cyanoborohydride (0.005 moles, 0.33 g). The mixture is reacted at r.t. for 10 days, acidified with methanol HCl to pH=2, and evaporated to dryness under vacuum. The residue is taken up with water (100 ml), washed with ethyl ether (100 ml), alkalinized with sodium carbonate and extracted with chloroform (3×100 ml). The resulting oil (1.3 g) is dissolved in methanol (50 ml) and treated with 85% phosphoric acid (0.0065 moles, 0.75 g), then evaporated to dryness under vacuum to obtain the product as a very light solid foam. Yield: 2 g (77%)--m.p.=150-156° C. ]589 (c=1, water)=+1.9

Workup

  1. customThe mixture is reacted at r.t. for 10 days
  2. customevaporated to dryness under vacuum
  3. washwashed with ethyl ether (100 ml)
  4. extractionextracted with chloroform (3×100 ml)
  5. dissolutionThe resulting oil (1.3 g) is dissolved in methanol (50 ml)
  6. customevaporated to dryness under vacuum
  7. customto obtain the product as a very light solid foam

Sources & evidence

ORD record
ord-5898dd9486af4dcbbc2797e822ceb0de
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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