Dichloromethane → HCID 11139540, compound

HRID 1110458Notes

Reaction equation

HRID 1110458 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])=O.C(Cl)Cl.S([O-])([O-])(=O)=O.[Na+].[Na+]>O.O1CCCC1>[OH:4][CH2:5][C@H:7]1[NH:10][C:9](=[O:11])[C@H:8]1[NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 12762148HCID 12762148, compound

Product 1

HCID 11139540HCID 11139540, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.63 g of sodium borohydride in 25 ml of water is added dropwise to a well stirred solution of 3.0 g of cis-(±)-4-(methoxycarbonyl)-3-[((phenylmethoxy)carbonyl)amino]-2-azetidinone in 190 ml of tetrahydrofuran. The addition is made over a period of 10 minutes while stirring in an ice bath. The reaction is stirred for 3 hours. Methylene dichloride (250 ml) is added followed by anhydrous sodium sulfate. A clear solution is obtained by filtration. The solvent is removed and the residue is dissolved in acetone. The solution is clarified by filtration and concentrated to give 2.84 g of the title compound. Physical characteristics are as follows: 13C NMR (δ, CH3OH-d6): 55.9, 60.2, 61.6 67.9, 128.7-129.3, 137.6, 158, 170.7.

Workup

  1. additionThe addition
  2. stirringThe reaction is stirred for 3 hours
  3. customA clear solution is obtained by filtration
  4. customThe solvent is removed
  5. dissolutionthe residue is dissolved in acetone
  6. filtrationThe solution is clarified by filtration
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-89bff0815bfc4981a461bbb62d589850
Source dataset
uspto-grants-1990_12
Patent number
US04975538

Reaction notes

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