Acetic Acid → HCID 54062313, compound

HRID 264602Notes

Reaction equation

HRID 264602 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C@H:6]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].N[C@H]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)CC([O-])=O.C(O)(=O)C.C([O-])(=O)C.[Na+].C(=O)C1C=CC=CC=1>CO.C(O)C>[CH2:26]([NH:5][C@H:6]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 53673982HCID 53673982, compoundHCID 57444810HCID 57444810, compound

Product 1

HCID 54062313HCID 54062313, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A total of 19.1 g of sodium cyanoborohydride (0.304 mol) is added in portions to a solution of 42.2 g (0.203 mmol) of ethyl (R)-3-amino-4-phenylbutyrate obtainable by esterification of the known (R)-3-amino-4-phenylbutyrate with ethanol, 11.6 ml (0.203 mol) of glacial acetic acid, 33.3 g (0.406 mol) of sodium acetate and 20.9 ml ((0.207 mol) of benzaldehyde in 400 ml of methanol at -5° to 5°. After the addition is complete, reaction is allowed to go to completion at room temperature for 1 hour. The yellow suspension is almost completely concentrated in a rotary evaporator, and the pasty residue is partitioned between ethyl acetate and water which is adjusted to about pH 8 with ammonia solution. The organic phases are washed with water and brine until neutral, dried over magnesium sulfate and evaporated to dryness, resulting in a yellow oil. This is chromatographed on silica gel with methylene chloride/methanol 99:1, resulting in the title compound of the formula as a pale yellow oil. The oxolate is obtained by adding oxalic acid to an ethereal solution of the title compound.

Workup

  1. additionAfter the addition
  2. customreaction
  3. concentrationThe yellow suspension is almost completely concentrated in a rotary evaporator
  4. customthe pasty residue is partitioned between ethyl acetate and water which
  5. washThe organic phases are washed with water and brine until neutral,
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customresulting in a yellow oil
  9. customThis is chromatographed on silica gel with methylene chloride/methanol 99:1

Sources & evidence

ORD record
ord-48853ec9a8914d4485e024c1e09dbbef
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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