Ammonia → HCID 131711850, compound

HRID 1856004Notes

Reaction equation

HRID 1856004 reaction equation
[C:1]([N:11]1[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C)C1C=CC=CC=1.C(Cl)(Cl)=O.N.[C:35]([N:45]1C[C@H](OC(Cl)=O)C[C@H]1C(OC)=O)(OCC1C=CC=CC=1)=[O:36]>C1(C)C=CC=CC=1>[C:1]([N:11]1[CH2:19][C@H:18]([O:20][C:35]([NH2:45])=[O:36])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 131711851HCID 131711851, compound

Product 1

HCID 131711850HCID 131711850, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of equivalent quantities of N-carbobenzyloxy-trans-4-hydroxy-L-proline, methyl ester from Example 1, part b, and dimethylaniline is treated with a solution of phosgene in toluene. After standing overnight an equivalent quantity of ammonia is passed through the solution of trans-N-carbobenzyloxy-4-[(chlorocarbonyl)oxy]-L-proline, methyl ester. After standing for twelve hours at room temperature, the solution is washed with water, dried over magnesium sulfate, filtered and the solvent evaporated to give trans-N-carbobenzyloxy-4-[(aminocarbonyl)oxy]-L-proline, methyl ester.

Workup

  1. waitAfter standing for twelve hours at room temperature
  2. washthe solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-f200641de1f740d3b594bd7ca1beb1fb
Source dataset
uspto-grants-1980_08
Patent number
US04217359

Reaction notes

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