Hydrochloric Acid → HCID 131719047, compound

HRID 1647912Notes

Reaction equation

HRID 1647912 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[N:16]1([C:24]([O:26][CH2:27][CH:28]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]3[C:29]2=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=O.Cl.[NH2:42][C@@H:43]([C:45]([NH2:47])=[O:46])[CH3:44].C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[N:16]1([C:24]([O:26][CH2:27][CH:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[C:40]2=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:25])[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH:42][C@@H:43]([C:45]([NH2:47])=[O:46])[CH3:44])=[O:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 446080(R)-2-aminopropanamideHCID 688135Fmoc-Pro-OH

Product 1

HCID 131719047HCID 131719047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3.36 g of DCC are added to a stirred solution of 5.4 g (16 mmol) of Fmoc-Pro-OH, 2 g of HCl.H-D-Ala-NH2 and 2.24 g of HOBt in 30 ml of dimethylformamide at 0° C. The mixture is left to stir at 0° C. for 1 hour and to stand at room temperature overnight. The precipitate is filtered off with suction and the filtrate is concentrated. The residue is dissolved in ethyl acetate and extracted by shaking successively with water, twice with saturated NaHCO3 solution, water, KHSO4 buffer and water. Fmoc-Pro-D-Ala-NH2 precipitates in the ethyl acetate phase during this and is filtered off with suction. The ethyl acetate mother liquor is concentrated and triturated with diethyl ether and filtered with suction.

Workup

  1. customat 0° C
  2. waitThe mixture is left
  3. waitto stand at room temperature overnight
  4. filtrationThe precipitate is filtered off with suction
  5. concentrationthe filtrate is concentrated
  6. dissolutionThe residue is dissolved in ethyl acetate
  7. extractionextracted
  8. stirringby shaking successively with water, twice with saturated NaHCO3 solution, water, KHSO4 buffer and water
  9. customFmoc-Pro-D-Ala-NH2 precipitates in the ethyl acetate phase during this and
  10. filtrationis filtered off with suction
  11. concentrationThe ethyl acetate mother liquor is concentrated
  12. customtriturated with diethyl ether
  13. filtrationfiltered with suction

Sources & evidence

ORD record
ord-85c676b3cd534ab88e6d4bee27fdb525
Source dataset
uspto-grants-1995_07
Patent number
US05434138

Reaction notes

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