Ammonia → HCID 18631928, compound

HRID 346353Notes

Reaction equation

HRID 346353 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:9]([O:12][CH2:13][C@@H:14]1[CH2:18][C@@H:17]([OH:19])[CH2:16][N:15]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21])([CH3:11])[CH3:10])([OH:8])=O.C([N:35](CC)CC)C.N>O1CCCC1.C(O)C.C(OCC)(=O)C>[C:6]([C:9]([O:12][CH2:13][C@@H:14]1[CH2:18][C@@H:17]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:16][N:15]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21])([CH3:11])[CH3:10])(=[O:8])[NH2:35]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18631929HCID 18631929, compound

Product 1

HCID 18631928HCID 18631928, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methanesulfonyl chloride (0.4 ml) in tetrahydrofuran (2 ml) was dropwise added to a solution of (2S,4R)-2-(1-carboxy-1-methylethyl)oxymethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.84 g) and triethylamine (1 ml) in tetrahydrofuran (8 ml) at -10°~-5° C. and the mixture was stirred at the same condition for 30 minutes. The mixture was dropwise added to a 10% solution (20 ml) of ammonia in ethanol and the mixture was stirred at the same temperature for 1 hour. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (50 ml), washed with water (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (1:99 V/V) to give (2S,4R)-2-(1-carbamoyl-1-methylethyl)oxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.01 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a residue
  4. washwashed with water (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of methanol and chloroform (1:99 V/V)

Sources & evidence

ORD record
ord-8959533b056f4040b1a68a55be20aaa0
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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