Trichloroacetic Acid → 81733-39-3

HRID 2290844Notes

Reaction equation

HRID 2290844 reaction equation
[CH2:1]1[CH:7]([OH:8])[NH:6][P:4]([N:9]([CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][Cl:12])(=[O:5])[O:3][CH2:2]1.[CH2:16]([O:18][C:19](=[O:22])[NH:20]O)[CH3:17].ClC(Cl)(Cl)C(O)=O>C(Cl)Cl>[CH2:16]([O:18][C:19](=[O:22])[NH:20][O:8][CH:7]1[CH2:1][CH2:2][O:3][P:4]([N:9]([CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][Cl:12])(=[O:5])[NH:6]1)[CH3:17]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 11510HydroxyurethaneHCID 997354-Hydroxycyclophosphamide

Product 1

HCID 306755181733-39-3

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

550 mg (2 mmol) of 4-hydroxycyclophosphamide and 210 mg (2 mmol) of ethylhydroxycarbamate (hydroxyurethane) are dissolved in 5 ml of dry methylenechloride free of alcohol. A catalytic amount of trichloroacetic acid and molecular sieve 4 A are added thereto. The reaction mixture is allowed to stand at -25° C. for 3 days. Thereafter, the molecular sieve is separated and washed once with a diluted solution of NaHCO3. The methylenechloride phase is dried over sodium sulfate and part of the solvent is evaporated in a vacuum and thereafter diluted with ether. After standing for 20 hours at -25° C., the separated crystals are filtered off, washed and dried.

Workup

  1. customThereafter, the molecular sieve is separated
  2. washwashed once with a diluted solution of NaHCO3
  3. dry with materialThe methylenechloride phase is dried over sodium sulfate and part of the solvent
  4. customis evaporated in a vacuum
  5. additiondiluted with ether
  6. waitAfter standing for 20 hours at -25° C.
  7. filtrationthe separated crystals are filtered off
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-9a579ecb76974f81b3bc4faafa18093d
Source dataset
uspto-grants-1986_10
Patent number
US04618692

Reaction notes

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