Hydrochloric Acid → HCID 70224589, compound

HRID 2258401Notes

Reaction equation

HRID 2258401 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C@H:19]([C:29]([O:31]C(C)(C)C)=[O:30])[CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])=[O:17])=[CH:11][CH:10]=1)[CH2:6][CH2:7][Cl:8]>CCOCC.C(OCC)(=O)C>[ClH:2].[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]([NH:18][C@H:19]([C:29]([OH:31])=[O:30])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:17])=[CH:13][CH:14]=1)[CH2:6][CH2:7][Cl:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10768231HCID 10768231, compound

Product 1

HCID 70224589HCID 70224589, compoundYield 186.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A saturated solution of hydrogen chloride in ether (120 ml) was added to a solution of ditertbutyl N-(-4-[N,N-bis-(2-chloroethyl)amino]-phenylcarbamoyl)-L-glutamate (4.4 g) in ethyl acetate (20 ml). After 1 hour at ambient temperature the mixture was evaporated to a solid. This solid was triturated with ether to obtain N-(4-[N,N-bis(2-chloroethyl)amino]phenylcarbamoyl)-L-glutamic acid hydrochloride (3.5 g) as a grey solid m.p=148°-150° C. (see Scheme 3)

Workup

  1. customAfter 1 hour at ambient temperature the mixture was evaporated to a solid
  2. customThis solid was triturated with ether

Sources & evidence

ORD record
ord-cb7465ab3f85418985e4a34fb60c2bf3
Source dataset
uspto-grants-1997_08
Patent number
US05660829

Reaction notes

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