Hydrochloric Acid → HCID 86747732, compound

HRID 1463540Notes

Reaction equation

HRID 1463540 reaction equation
[Na+].[Na+].[Na+].C(OC([NH:11][C@H:12]([C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:43])([P:39]([O-:42])(=[O:41])[OH:40])[P:35]([O-:38])(=[O:37])[O-:36])=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH2:24][CH2:25][Cl:26])[CH2:21][CH2:22][Cl:23])=[CH:16][CH:15]=1)=O)(C)(C)C.Cl>CO>[ClH:23].[Cl:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][Cl:26])[C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@@H:12]([C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:43])([P:35]([OH:38])(=[O:36])[OH:37])[P:39]([OH:42])(=[O:40])[OH:41])=[O:28])[NH2:11])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131718376HCID 131718376, compound

Product 1

HCID 86747732HCID 86747732, compoundYield 174.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-{N'-(tert-butoxycarbonyl)-4-[bis(2-chloroethyl)amino]-(L)-phenylalanyl}-5-amino-1-hydroxypentane-1,1-diphosphonic acid trisodium salt (35 mg) in methanol saturated with hydrochloric acid (2 ml) is heated to 40°-50° C. for 4 hours, then the solution is concentrated to reduced volume and the precipitated sodium chloride is filtered. The filtrate is evaporated to dryness and the residue is triturated with acetone and filtered. After recrystallization from ethanol/ethyl ether, N-{4-[bis(2-chloroethyl)amino]-(L)-phenylalanyl}-5-amino-1-hydroxypentane-1,1-diphosphonic acid monohydrochloride (25 mg) is obtained, m.p. >260° C., [α]D =+7.9 (c=2, methanol), NMR (TMS, D2O): 1.25÷1.40 (m, 2H), 1.42÷1.72 (m, 2H); 1.8÷2.06 (m, 2H); 2.9÷3.2 (m, 4H); 3.65 (t, 4H); 4.0 (t, 4H); 4.1 (t, 1H); 7.35 (s, 4H).

Workup

  1. concentrationthe solution is concentrated to reduced volume
  2. filtrationthe precipitated sodium chloride is filtered
  3. customThe filtrate is evaporated to dryness
  4. customthe residue is triturated with acetone
  5. filtrationfiltered
  6. customAfter recrystallization from ethanol/ethyl ether

Sources & evidence

ORD record
ord-40ee176de4cb421eb272fa03f3757cd1
Source dataset
uspto-grants-1994_04
Patent number
US05300671

Reaction notes

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