Trichloroacetic Acid → Carbamic acid, ((2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazap hosphorin-4-yl)oxy)-, phenylmethyl ester, P-oxide

HRID 2290845Notes

Reaction equation

HRID 2290845 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:23][C:24](=[O:27])[NH:25]O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClC(Cl)(Cl)C(O)=O>C(Cl)Cl>[CH2:16]([O:23][C:24](=[O:27])[NH:25][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)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 18907Benzyl hydroxycarbamateHCID 997354-Hydroxycyclophosphamide

Product 1

HCID 3067552Carbamic acid, ((2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazap hosphorin-4-yl)oxy)-, phenylmethyl ester, P-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

750 mg (2.7 mmol) of 4-hydroxycyclophosphamide and 450 mg (2.7 mmol) of benzyl-hydroxycarbamate are dissolved in 6 ml of methylene chloride free of alcohol. A small amount of trichloroacetic acid is added thereto and the solution is allowed to stand at -25° C. in a refrigerator for 3 days. The resulting solution is filtered off, the mother liquor is diluted with 5 ml of chloroform, then is diluted with water and thereafter is washed with a dilute solution of NaHCO3 and with water. The washed solution is dried over sodium sulfate and is evaporated in a vacuum. The oily residue thereafter is recrystallized from acetic acid ethyl ester containing a small amount of methanol.

Workup

  1. filtrationThe resulting solution is filtered off
  2. additionthe mother liquor is diluted with 5 ml of chloroform
  3. additionis diluted with water
  4. washis washed with a dilute solution of NaHCO3 and with water
  5. dry with materialThe washed solution is dried over sodium sulfate
  6. customis evaporated in a vacuum
  7. customThe oily residue thereafter is recrystallized from acetic acid ethyl ester containing a small amount of methanol

Sources & evidence

ORD record
ord-b3984a1affbf495190654f9ef75af39a
Source dataset
uspto-grants-1986_10
Patent number
US04618692

Reaction notes

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