Propylamine → Benzyl 6-(1-hydroxyethyl)-6-methyl-3-propylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 247491Notes

Reaction equation

HRID 247491 reaction equation
[OH:1][CH:2]([C:4]1([CH3:23])[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](Cl)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3].C(N(CC)CC)C.[CH2:31]([NH2:34])[CH2:32][CH3:33]>CN(C=O)C.C(OCC)(=O)C>[OH:1][CH:2]([C:4]1([CH3:23])[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([NH:34][CH2:31][CH2:32][CH3:33])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 15136305Benzyl 6-(1-hydroxyethyl)-6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 20160993Benzyl 6-(1-hydroxyethyl)-6-methyl-3-propylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 6-(1-hydroxyethyl)-6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (50 mg) in anhydrous DMF (1 ml) is cooled in an ice-bath and stirred while triethylamine (28 μl) and propylamine (12.4 μl) are added. The resulting solution is allowed to slowly warm to room temperature and kept at room temperature for 1 hr. The solution is diluted with ethyl acetate (10 ml), washed with water (5×2 ml), pH 3 phosphate buffer (2 ml), 5% NaHCO3 (2 ml), and brine, dried with MgSO4, filtered, and evaporated in vacuo to give benzyl 6-(1-hydroxyethyl)-6-methyl-3-propylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. additionare added
  2. washwashed with water (5×2 ml), pH 3 phosphate buffer (2 ml), 5% NaHCO3 (2 ml), and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-34f95e564f74448189de13a20eb18b3d
Source dataset
uspto-grants-1987_11
Patent number
US04707547

Reaction notes

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