Morpholine → HCID 70503522, compound

HRID 67835Notes

Reaction equation

HRID 67835 reaction equation
[CH2:1]([C:8]1[S:14][CH:13]2[CH:10]([C:11](=[O:32])[N:12]2[C:15](=[C:29](O)[CH3:30])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.[Br:44]N1C(=O)CCC1=O.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:1]([C:8]1[S:14][CH:13]2[CH:10]([C:11](=[O:32])[N:12]2[C:15](=[C:29]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH2:30][Br:44])[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 8083MorpholineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31297Methanesulfonyl chlorideHCID 67184N-bromobutanimideHCID 70503680p-Nitrobenzyl alpha-(3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-alpha-(1-hydroxyethylidene)acetate

Product 1

HCID 70503522HCID 70503522, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

One dissolves p-nitrobenzyl α-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate (827 mg) in methylene chloride (10 ml), cools to -20° C., adds a solution of methanesulfonyl chloride (1 M in methylene chloride; 2.2 ml) and a solution of triethylamine (1 M in methylene chloride; 2.2 ml), stirs for 90 minutes, cools to -25° C., adds morpholine (0.35 ml), stirs for 65 minutes, adds N-bromosuccinimide (340 mg), and stirs for 1 hour. One washes the reaction mixture with water, dries over magnesium sulfate, and evaporates. Purification of the obtained residue by chromatography over silica gel containing 10% water (30 g) gives p-nitrobenzyl α-[3-benzyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-morpholino-2-bromoethylidene)acetate (710 mg). Yield: 65%.

Workup

  1. customcools to -20° C.
  2. customevaporates
  3. customPurification of the obtained residue by chromatography over silica gel containing 10% water (30 g)

Sources & evidence

ORD record
ord-21896339ae8a45238dbb56a4a3c8b3f7
Source dataset
uspto-grants-1982_08
Patent number
US04346218

Reaction notes

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