Hydrochloric Acid → HCID 86740867, compound

HRID 1982629Notes

Reaction equation

HRID 1982629 reaction equation
Cl.C[C:3](C)([O:5][C:6](=[O:33])[CH2:7][NH:8][CH2:9][CH:10]([NH:15][C:16]([CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])C>CO>[CH3:3][O:5][C:6](=[O:33])[CH2:7][NH:8][CH2:9][CH:10]([NH:15][C:16]([CH:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86740868HCID 86740868, compound

Product 1

HCID 86740867HCID 86740867, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 50 ml of methanol, saturated with hydrogen chloride gas is added 1.77 g of [S-(R*,R*)]-2-[[[1-[[[-2-(1,1-dimethylethoxy)-2-oxoethyl]amino]methyl]-3-methylbutyl]amino]carbonyl]-1-pyrrolidinecarboxylic acid, phenylmethyl ester in 10 ml of methanol. After standing at room temperature for four hours, the solution is kept at 0° overnight. The solvent is then removed under reduced pressure and the residue taken up in ethyl acetate. The ethyl acetate solution is washed two times with saturated sodium bicarbonate solution, once with saturated sodium chloride solution, and then dried over magnesium sulfate. Removal of the solvent under reduced pressure gives 1.14 g of [S-(R*,R*)]-2-[[[1-[[(2-methoxy-2-oxoethyl)amino]methyl]-3-methylbutyl]amino]carbonyl]-1-pyrrolidinecarboxylic acid, phenylmethyl ester.

Workup

  1. waitthe solution is kept at 0° overnight
  2. customThe solvent is then removed under reduced pressure
  3. washThe ethyl acetate solution is washed two times with saturated sodium bicarbonate solution
  4. dry with materialonce with saturated sodium chloride solution, and then dried over magnesium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b833a7ccaaa745e6bb75728b62dfd3b0
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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