Hydrochloric Acid → HCID 21622695, compound

HRID 1440657Notes

Reaction equation

HRID 1440657 reaction equation
[NH2:1][P:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[OH:3].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C.Cl>O>[CH2:13]([O:20][C:21]([NH:1][P:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[OH:4])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 67676182HCID 67676182, compound

Product 1

HCID 21622695HCID 21622695, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Compound 2 (1.1 g, 6 mmole) is dissolved in 10 ml of water and then the pH of this solution is adjusted to 9.5 with the aid of a 4N soda solution. To this mixture cooled in an icebath is gently added benzylchloroformate (1.2 ml, 7.5 mmole), whilst maintaining the pH of the reaction at 9.5 by successive soda additions. Stirring of the reaction mixture is maintained at 0° C. for 30 min. and then for 1 h at ambient temperature. After diethyl ether treatment, the mixture is cooled, and then acidified by the addition of hydrochloric acid. The product which precipitates is filtered, washed with cold water and dried. The expected compound 3 is obtained with a 76% yield (1.5 g), RF(1)=0.57, RF(2)=0.76, m.p. 110° C.

Workup

  1. temperatureTo this mixture cooled in an icebath
  2. temperaturewhilst maintaining
  3. customthe pH of the reaction at 9.5 by successive soda additions
  4. customThe product which precipitates
  5. filtrationis filtered
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-51bb8f303d4e4c5e9e3a2c653346f05f
Source dataset
uspto-grants-1996_03
Patent number
US05500414

Reaction notes

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