Hydrochloric Acid → HCID 20719101, compound

HRID 848721Notes

Reaction equation

HRID 848721 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].CCN(CC)CC.ClC(O[CH2:30][CH:31]([CH3:33])[CH3:32])=O.N[C@H](C(O)=O)CC(C)C.Cl>C1COCC1.O.CC(O)=O>[CH2:12]([O:11][C:9]([N:1]([CH2:8][CH2:7][CH3:6])[C@H:2]([C:3]([OH:5])=[O:4])[CH2:30][CH:31]([CH3:33])[CH3:32])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 20719101HCID 20719101, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

12.5 g (0.05 mol) of Cbz-Pro are dissolved in 70 cc of THF and 7.5 cc (0.05 mol) of Et3N, and then cooled to -10° C. 6.8 g (0.05 mol) of isobutyl chloroformate in 30 cc of THF are added dropwise, whereafter the mixture is stirred for 20 minutes at <10° C. A solution of 7.9 g (0.06 mol) of Leu and 12.6 cc (0.08 mol) of Et3N in 65 cc of water are added to the mixture and the reaction is allowed to continue for 90 minutes, allowing the temperature to rise to 20° C. The reaction mixture is acidified with 6N-HCl, the THF is removed under vacuum and the solid which is obtained is dissolved in 20 cc of AcOH and then precipitated with 200 cc of water. Recrystallisation takes place in CCl4. The product indicated in the heading is obtained, this having two melting points: either 118° C. or 136° C.

Workup

  1. waitto continue for 90 minutes
  2. customto rise to 20° C
  3. customthe THF is removed under vacuum
  4. customthe solid which is obtained
  5. customprecipitated with 200 cc of water
  6. customRecrystallisation
  7. customis obtained
  8. customeither 118° C. or 136° C.

Sources & evidence

ORD record
ord-e6952f7add724ea791692d38948487a5
Source dataset
uspto-grants-1981_10
Patent number
US04297346

Reaction notes

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