Dichloromethane → HCID 86737254, compound

HRID 903199Notes

Reaction equation

HRID 903199 reaction equation
[O:1]=[C:2]1[CH:5]([N:6]=[N+:7]=[N-:8])[CH:4]([CH2:9][CH2:10][C:11](=[O:14])[CH2:12][OH:13])[N:3]1[CH:15]([P:32]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])=[O:33])[C:16]([O:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(Cl)Cl.[CH3:43][S:44](Cl)(=[O:46])=[O:45].O=C1C(N=[N+]=[N-])C(CCC(=O)COS(C)(=O)=O)N1C(P(OCC)(OCC)=O)C([O-])=O>C(N(CC)CC)C>[O:1]=[C:2]1[CH:5]([N:6]=[N+:7]=[N-:8])[CH:4]([CH2:9][CH2:10][C:11](=[O:14])[CH2:12][O:13][S:44]([CH3:43])(=[O:46])=[O:45])[N:3]1[CH:15]([P:32]([O:34][CH2:35][CH3:36])([O:37][CH2:38][CH3:39])=[O:33])[C:16]([O:18][CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86737255HCID 86737255, compoundHCID 86737256HCID 86737256, compound

Product 1

HCID 86737254HCID 86737254, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Benzhydryl (2-oxo3-azido-4-[3-keto-4-hydroxybutyl]-N-azetidinyl)diethylphosphonoacetate, 251 mg., is treated at 0° under N2 in 22 ml. CH2Cl2 with 0.056 ml. methanesulfonyl chloride for 5 min., and then .100 ml. triethylamine is added. After 2 min. more at 0° and 30 min. at 25°, the solvent is evaporated and the product chromatographed by PLC, eluting with 10:3 CHCl3 -acetone, affording 197 mg. pure benzyhydryl (2-oxo-3-azido-4-[3-keto-4-methanesulfonyloxybutyl]-N-azetidinyl)diethylphosphonoacetate. NMR (δ, CDCl3): 1.24 m, POCH2CH3 ; 2.0-2.5 m, CH2CH2 ; 3.14 s, CH3SO2 ; 3.8-4.4 m, POCH2CH3 ; 4.71 s, COCH2OSO2Me; 5.09 d, J=22, CHP; 6.93 s, CHφ2 ; 7.36 s, Ar. IR (μ, film): 4.73, azido; 5.64, β-lactam; 5.72, ester.

Workup

  1. addition, is treated at 0° under N2 in 22 ml
  2. custom30 min. at 25°, the solvent is evaporated
  3. customthe product chromatographed by PLC
  4. washeluting with 10:3 CHCl3 -acetone
  5. customaffording 197 mg
  6. custom3.14 s, CH3SO2
  7. custom4.71 s, COCH2OSO2Me
  8. custom5.09 d, J=22, CHP
  9. custom6.93 s, CHφ2
  10. custom7.36 s, Ar

Sources & evidence

ORD record
ord-6d60340807114f7fa4b9ae98779dc254
Source dataset
uspto-grants-1980_10
Patent number
US04226866

Reaction notes

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