Ammonia → HCID 70468784, compound

HRID 1982646Notes

Reaction equation

HRID 1982646 reaction equation
C([O:3][C:4]([CH2:6][NH:7][C:8]([CH2:10][O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:9])=O)C.[NH3:28]>C(O)C>[NH2:28][C:4](=[O:3])[CH2:6][NH:7][C:8]([CH2:10][O:11][CH2:12][C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:9]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53809668HCID 53809668, compound

Product 1

HCID 70468784HCID 70468784, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-Phenylmethyl 2-[[[[[(ethoxycarbonyl)methyl]amino]carbonyl]methoxy]methyl]-1-pyrrolidinecarboxylate, 4 g (0.01057 mol), is dissolved in 100 ml of ethanol and the solution saturated with ammonia at room temperature. The solution is allowed to stand at room temperature for five days, the solvent evaporated in vacuo and the residue dissolved in 100 ml of methanol and the solution saturated with ammonia at room temperature. The solution is allowed to stand at room temperature for 14 hours and the solvent evaporated in vacuo. The residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (90:10) to give (S)-phenylmethyl 2-[[[[(2-amino-2-oxoethyl)amino]carbonyl]methoxy]methyl]-1-pyrrolidinecarboxylate, 3 g; mp 109.5°-111°; [α]D25 -41.0° (c 0.57, methanol).

Workup

  1. customat room temperature
  2. customthe solvent evaporated in vacuo
  3. dissolutionthe residue dissolved in 100 ml of methanol
  4. customat room temperature
  5. waitto stand at room temperature for 14 hours
  6. customthe solvent evaporated in vacuo
  7. customThe residue is purified by chromatography
  8. washeluting with dichloromethane-methanol (90:10)

Sources & evidence

ORD record
ord-28b9281e185f4e2bb6ea2a30e369aab4
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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