Hydrochloric Acid → HCID 22805892, compound

HRID 1112724Notes

Reaction equation

HRID 1112724 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[OH:21][CH:22]1[CH2:26][NH:25][C@H:24]([C:27]([OH:29])=[O:28])[CH2:23]1.Cl>CCOCC.O>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:25]1[CH2:26][CH:22]([OH:21])[CH2:23][C@H:24]1[C:27]([OH:29])=[O:28])=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 69248L-Proline, 4-hydroxy-, cis-HCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 22805892HCID 22805892, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

24.05 g (0.121 mol) of o-acetoxybenzoyl chloride in 50 ml of anhydrous ether, and 17 ml (0.121 mol) of pure triethylamine in 18 ml of iced water, were added simultaneously over the course of 0.5 hr, at -2° C. ± 1° C., whilst stirring so as to produce emulsification, to a solution of 15.9 g (0.121 mol) of 4-hydroxy-L-proline in 42 ml of water and 17 ml (0.121 mol) of pure triethylamine. Stirring was continued for 0.75 hr at the same temperature and then for 25 minutes at ambient temperature. The pH was reduced from 7 to 3 by adding 9.8 ml of 12.35 N HCl (0.121 mol). The milky cloudiness was extracted with a total of 900 ml of pure ethyl acetate and the combined organic extracts were dried over anhydrous Na2SO4 and then concentrated in vacuo to give, in 2 to 3 successive crops, 23 g of the desired product (65% yield).

Workup

  1. customto produce emulsification
  2. stirringStirring
  3. waitfor 25 minutes at ambient temperature
  4. extractionThe milky cloudiness was extracted with a total of 900 ml of pure ethyl acetate
  5. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c20a871c72594110a9030ad5d0c644da
Source dataset
uspto-grants-1978_10
Patent number
US04123544

Reaction notes

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