Ammonia → HCID 10563557, compound

HRID 2371391Notes

Reaction equation

HRID 2371391 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:22](CC)CC)C.ClC(OC(CC)C)=O.N>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([NH2:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 11829505sec-Butyl chloroformate

Product 1

HCID 10563557HCID 10563557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

trans-1-Benzyloxycarbonyl-4-hydroxy-L-proline (3.55 g) was dissolved in dry tetrahydrofuran (60 ml), and triethylamine (2.80 ml) was added thereto, followed by addition of sec-butyl chloroformate (2.75 g) at 0° to 5° C. under nitrogen stream. The resultant mixture was stirred at the same temperature for 30 minutes and cooled to -50° C. 28 Aqueous ammonia (3.62 ml) was added thereto, and the resulting mixture was stirred at the same temperature for 30 minutes, followed by removal of the solvent. The residue was diluted with ethyl acetate and dried over magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give (2S,4R)-1-benzyloxycarbonyl-2-aminocarbonyl-4-hydroxypyrrolidine.

Workup

  1. customfollowed by removal of the solvent
  2. additionThe residue was diluted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d9dbeb0509d464f9a70f9f61bc9d58f
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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