Ammonia → HCID 54526147, compound

HRID 1982636Notes

Reaction equation

HRID 1982636 reaction equation
COC(Cl)=O.[C:6]1([CH2:12][CH:13]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:14][O:15][CH2:16][C:17](O)=[O:18])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([N:33](CC)CC)C.N>ClCCl>[C:25]1([CH2:24][O:23][C:21](=[O:22])[NH:20][CH:13]([CH2:14][O:15][CH2:16][C:17]([NH2:33])=[O:18])[CH2:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 23316622HCID 23316622, compound

Product 1

HCID 54526147HCID 54526147, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Methylchloroformate, 0.89 g (0.0094 mol) is added dropwise with stirring to a solution of 2.75 g (0.008 mol) of (±)-[3-phenyl-2-[[(phenylmethoxy)carbonyl]amino]propoxy]acetic acid and 0.96 g (0.0095 mol) of triethylamine in 100 ml of dichloromethane at -5°-10° C. The mixture is stirred for 30 minutes at -5° C., allowed to reach 0° C. and saturated with ammonia for 5 minutes. The mixture is allowed to reach room temperature and stirred for one hour, the solvent is evaporated in vacuo, the residue dissolved in 200 ml of dichloromethane, washed with a saturated aqueous solution of sodium chloride, 2×200 ml, the dichloromethane layer separated, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by chromatography using silica gel and eluting with dichloromethane-methanol (95:5) to give (±)-phenylmethyl-[1-[(2-amino-2-oxoethoxy)methyl]-2-phenylethyl]carbamate, 2.5 g; mp 135°-137°.

Workup

  1. customto reach room temperature
  2. stirringstirred for one hour
  3. customthe solvent is evaporated in vacuo
  4. dissolutionthe residue dissolved in 200 ml of dichloromethane
  5. washwashed with a saturated aqueous solution of sodium chloride, 2×200 ml
  6. customthe dichloromethane layer separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue is purified by chromatography
  10. washeluting with dichloromethane-methanol (95:5)

Sources & evidence

ORD record
ord-f02eac06bcc4482e9c2c13c17c8cef07
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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